Mercapto-imidazolyl derivatives

ABSTRACT

The present invention provides mercapto-imidazolyl compounds, and the acid addition salts and metal salt complexes thereof; a process for their preparation; and a method for their use as microbicides.

TECHNICAL FIELD OF THE INVENTION

The present invention relates to new mercapto-imidazolyl derivatives, toa plurality of processes for their preparation, and to their use asmicrobicides.

BACKGROUND OF THE INVENTION

It has already been disclosed that a large number-of imidazolylderivatives have fungicidal properties (cf. EP-A 0 015 756, EP-A 0 040345, EP-A 0 052 424, EP-A 0 061 835, EP-A 0 297 345, EP-A 0 094 564,EP-A 0 196 038, EP-A 0 267 778, EP-A 0 378 953, EP-A 0 044 605, EP-A 0069 442, EP-A 0 055 833, EP-A 0 301 393, DE-A 2 324 010, DE-A 2 737 489,DE-A 2 551 560, EP-A 0 065 485, DE-A 2 735 872, EP-A 0 234 242, DE-A 2201 063, EP-A 0 145 294 and DE-A 3 721 786). While the activity of thesesubstances is good, it leaves something to be desired in some cases atlow rates of application.

DETAILED DESCRIPTION OF THE INVENTION

There have now been found new mercapto-imidazolyl derivatives of theformula ##STR1## in which R represents hydrogen or alkyl having 1 to 4carbon atoms and

R¹ represents a radical of the formula ##STR2##

where

R² and R³ are identical or different and represent optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted cycloalkyl, optionally substituted aralkyl, optionallysubstituted aralkenyl, optionally substituted aroxyalkyl, optionallysubstituted aryl or optionally substituted heteroaryl,

or

R¹ represents a radical of the formula ##STR3##

where

R⁴ represents alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 7carbon atoms which is optionally substituted by halogen, or representsnaphthyl, or represents phenyl which is optionally monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen, nitro, phenyl, phenoxy, alkyl having 1 to 4carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4carbon atoms and 1 to 5 halogen atoms and/or halogenoalkylthio having 1to 4 carbon atoms and 1 to 5 halogen atoms, and

R⁵ represents phenyl which is optionally monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5halogen atoms and/or halogenoalkylthio having 1 to 4 carbon atoms and 1to 5 halogen atoms,

or

R¹ represents a radical of the formula ##STR4##

where

R⁶ and R⁷ independently of one another represent hydrogen or alkylhaving 1 to 6 carbon atoms,

X¹ represents halogen, alkyl having 1 to 5 carbon atoms, alkoxy having 1to 4 carbon atoms, phenyl, phenoxy, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbonatoms and 1 to 5 halogen atoms, or represents halogenoalkylthio having 1to 4 carbon atoms and 1 to 5 halogen atoms, and

m represents the numbers 0, 1 or 2,

or

R¹ represents a radical of the formula ##STR5##

where

R⁸ and R⁹ independently of one another represent hydrogen or alkylhaving 1 to 6 carbon atoms,

X² represents halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbonatoms and 1 to halogen atoms, or phenyl,

n represents the numbers 0 or 1, and

p represents the numbers 0, 1 or 2,

or

R¹ represents a radical of the formula ##STR6##

where

R¹⁰ represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 6 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 6carbon atoms which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms, or represents optionally substituted aryl,or represents optionally substituted aralkyl,

or

R¹ represents a radical of the formula ##STR7##

where

R¹¹ represents hydrogen, alkyl or optionally substituted cycloalkyl,

X³ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms,

q represents the numbers 0, 1, 2 or 3 and

Y¹ represents an oxygen atom, a CH₂ group or a direct bond,

or

R¹ represents a radical of the formula ##STR8##

where

R¹² represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 7carbon atoms which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms, or represents cycloalkylalkyl having 3 to 7carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in thealkyl moiety, or represents phenyl which is optionally substituted byhalogen, or represents benzyl which is optionally substituted byhalogen,

X⁴ represents halogen, nitro, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms,phenyl which is optionally substituted by halogen and/or alkyl having 1to 4 carbon atoms, or represents phenoxy which is optionally substitutedby halogen and/or alkyl having 1 to 4 carbon atoms,

r represents the numbers 0, 1, 2 or 3 and

Y² represents an oxygen atom or a CH₂ group,

or

R¹ represents a radical of the formula ##STR9##

where

A represents alkanediyl having 2 or 3 carbon atoms which is optionallysubstituted by halogen and/or alkyl having 1 to 4 carbon atoms,

X⁵ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms,

and

s represents the numbers 0, 1, 2 or 3,

or

R¹ represents a radical of the formula ##STR10##

where

R¹³ represents alkyl having 1 to 10 carbon atoms, halogenoalkyl having 1to 6 carbon atoms and 1 to 5 halogen atoms, fluoroalkoxyalkyl having 1to 4 carbon atoms in the fluoroalkoxy moiety and 1 to 4 carbon atoms inthe alkyl moiety, cycloalkyl having 3 to 7 carbon atoms which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkylmoiety and 1 to 4 carbon atoms in the alkyl moiety, phenyl which isoptionally substituted by halogen, or phenylalkyl which has 1 to 4carbon atoms in the alkyl moiety and is optionally substituted byhalogen,

X⁶ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms, and t represents the numbers 0,1, 2 or 3,

or

R¹ represents a radical of the formula ##STR11##

where

R¹⁴ represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 7carbon atoms which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atomsin the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety,phenyl which is optionally substituted by halogen or benzyl which isoptionally substituted by halogen,

X⁷ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms,

u represents the numbers 0, 1, 2 or 3 and

Y³ represents an oxygen atom or a CH₂ group,

or

R¹ represents a radical of the formula ##STR12##

where

R¹⁵ represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 6 carbon atoms and 1 to 5 halogen atoms, optionally substituted arylor optionally substituted aralkyl,

X⁸ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms and

v represents the numbers 0, 1, 2 or 3,

and their acid addition salts and metal salt complexes.

A large number of substances according to the invention comprise one ormore asymmetrically substituted carbon atoms. They can therefore beobtained in the form of optical isomers. The present invention relatesto the individual isomers and also to mixtures of these.

Furthermore, it has been found that mercapto-imidazolyl derivatives ofthe formula (I) and their acid addition salts and metal salt complexesare obtained when imidazoles of the formula ##STR13## in which R¹ hasthe abovementioned meanings

are either

a) reacted in succession with strong bases and sulphur in the presenceof a diluent and the product is then hydrolysed with water, ifappropriate in the presence of an acid,

or

b) reacted with sulphur in the presence of a diluent of high boilingpoint and, if appropriate, the product is then treated with water and,if appropriate, with acid,

and the compounds of the formula ##STR14## in which R¹ has theabovementioned meanings

which are formed by variants (a) and (b), are, if appropriate, reactedwith halogen compounds of the formula

    R.sup.16 --HaI                                             (III)

in which

R¹⁶ represents alkyl having 1 to 4 carbon atoms and

HaI represents chlorine, bromine or iodine

in the presence of an acid binder and in the presence of a diluent, and,if appropriate, the resulting compounds of the formula (I) aresubsequently subjected to an addition reaction with an acid or a metalsalt.

Finally, it has been found that the new mercapto-imidazolyl derivativesof the formula (I) and their acid addition salts and metal saltcomplexes have very good microbicial properties and can be employed bothin crop protection and in the protection of materials.

Surprisingly, the substances according to the invention have a bettermicrobicidal activity than the prior-art compounds of the same directionof action which are most similar constitutionally.

Formula (I) provides a general definition of the mercapto-imidazolylderivatives according to the invention.

R preferably represents hydrogen, methyl, ethyl, n-propyl or isopropyl.

R¹ preferably represents a radical of the formula ##STR15## in which R²preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, it being possible for these radicals to be monosubstitutedto tetrasubstituted by identical or different substituents from theseries consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety and/orcycloalkyl having 3 to 7 carbon atoms, or

represents straight-chain or branched alkenyl having 2 to 6 carbonatoms, it being possible for each of these radicals to bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of halogen, alkoxy having 1 to 4 carbon atomsand/or cycloalkyl having 3 to 7 carbon atoms, or

represents cycloalkyl having 3 to 7 carbon atoms, it being possible foreach of these radicals to be monosubstituted to trisubstituted byidentical or different substituents from the series consisting ofhalogen, cyano and/or alkyl having 1 to 4 carbon atoms, or

represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1to 4 carbon atoms in the straight-chain or branched alkyl moiety, itbeing possible for the aryl moiety to be in each case monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand/or cyano, or

represents aralkenyl having 6 to 10 carbon atoms in the aryl moiety and2 to 4 carbon atoms in the alkenyl moiety, it being possible for thearyl moiety to be in each case monosubstituted to trisubstituted byidentical or different substituents from the series consisting ofhalogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbonatoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand/or cyano, or

represents aroxyalkyl having 6 to 10 carbon atoms in the aryl moiety and1 to 4 carbon atoms in the straight-chain or branched oxyalkyl moiety,it being possible for the aryl moiety to be in each case monosubstitutedto trisubstituted by identical or different substituents from the seriesconsisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand/or cyano, or

represents aryl having 6 to 10 carbon atoms, it being possible for eachof these radicals to be monosubstituted to trisubstituted by identicalor different substituents from the series consisting of halogen, alkylhaving 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthiohaving 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and/or cyano, or

represents an optionally benzo-fused, five- or six-memberedheteroaromatic radical having 1 to 3 hetero atoms such as nitrogen,sulphur and/or oxygen, it being possible for each of these radicals tobe monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of halogen, alkyl having 1 to 4carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinylhaving 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms,

alkylthio having 1 or 2 carbon atoms, halogenoalkyl, halogenoalkoxy andhalogenoalkylthio, each of which has 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms such as fluorine or chlorine atoms,formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxy group,acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety, nitroand/or cyano, and

R³ preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, it being possible for these radicals to be monosubstitutedto tetrasubstituted by identical or different substituents from theseries consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety and/orcycloalkyl having 3 to 7 carbon atoms, or

represents straight-chain or branched alkenyl having 2 to 6 carbonatoms, it being possible for each of these radicals to bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of halogen, alkoxy having 1 to 4 carbon atomsand/or cycloalkyl having 3 to 7 carbon atoms, or

represents cycloalkyl having 3 to 7 carbon atoms, it being possible foreach of these radicals to be monosubstituted to trisubstituted byidentical or different substituents from the series consisting ofhalogen, cyano and/or alkyl having 1 to 4 carbon atoms, or

represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1to 4 carbon atoms in the straight-chain or branched alkyl moiety, itbeing possible for the aryl moiety to be in each case monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen atoms, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and/or cyano, or

represents aralkenyl having 6 to 10 carbon atoms in the aryl moiety and2 to 4 carbon atoms in the alkenyl moiety, it being possible for thearyl moiety to be in each case monosubstituted to trisubstituted byidentical or different substituents from the series consisting ofhalogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbonatoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand/or cyano, or

represents aroxyalkyl having 6 to 10 carbon atoms in the aryl moiety and1 to 4 carbon atoms in the straight-chain or branched oxyalkyl moiety,it being possible for the aryl moiety to be in each case monosubstitutedto trisubstituted by identical or different substituents from the seriesconsisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand/or cyano, or

represents aryl having 6 to 10 carbon atoms, it being possible for eachof these radicals to be monosubstituted to trisubstituted by identicalor different substituents from the series consisting of halogen, alkylhaving 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthiohaving 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and/or cyano, or

represents an optionally benzo-fused, five- or six-memberedheteroaromatic radical having 1 to 3 hetero atoms such as nitrogen,sulphur and/or oxygen, it being possible for each of these radicals tobe monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of halogen, alkyl having 1 to 4carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinylhaving 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthiohaving 1 or 2 carbon atoms, halogenoalkyl, halogenoalkoxy andhalogenoalkylthio, each of which has 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms such as fluorine or chlorine atoms,formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxy group,acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety, nitroand/or cyano.

R¹ furthermore preferably represents a radical of the formula ##STR16##

in which

R⁴ preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, iso-butyl, tert-butyl, fluoro-tert-butyl,difluoro-tert-butyl, cycloalkyl having 3 to 6 carbon atoms which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/orbromine, or represents naphthyl, or represents phenyl which can bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, nitro,phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy,trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl,trifluoromethoxy, difluoromethoxy and/or trifluoromethylthio, and

R⁵ preferably represents phenyl which can be monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine, methyl, ethyl, isopropyl,tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxyand/or trifluoromethylthio.

R¹ furthermore preferably represents a radical of the formula ##STR17##

in which

R⁶ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁷ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X¹ preferably represents fluorine, chlorine, bromine, methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy,ethoxy, phenyl, phenoxy, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy or trifluoromethylthio and

m also preferably represents the numbers 0, 1 or 2,

it being possible for X¹ to represent identical or different radicals ifm represents 2.

R¹ furthermore preferably represents a radical of the formula ##STR18##

in which

R⁸ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁹ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X² preferably represents fluorine, chlorine, bromine, cyano, nitro,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, trichloromethoxy, trifluoromethoxy, difluoromethoxy,difluorochloromethoxy or phenyl,

n also preferably represents the numbers 0 or 1 and

p also preferably represents the numbers 0, 1 or 2,

it being possible for X² to represent identical or different radicals ifp represents 2.

R¹ furthermore preferably represents a radical of the formula ##STR19##

in which

R¹⁰ preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,cycloalkyl having 3 to 6 carbon atoms which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methyl and/orethyl, or represents phenyl, benzyl or phenethyl, it being possible foreach of the three last-mentioned radicals to be monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, or phenoxy which is optionally substituted by halogen and/oralkyl having 1 to 4 carbon atoms.

R¹ furthermore preferably represents a radical of the formula ##STR20##

in which

R¹¹ preferably represents hydrogen, straight-chain or branched alkylhaving 1 to 12 carbon atoms, or cycloalkyl having 3 to 7 carbon atomswhich is optionally monosubstituted to trisubstituted by identical ordifferent substituents from the series consisting of halogen and/oralkyl having 1 to 4 carbon atoms,

X³ preferably represents fluorine, chlorine, bromine, methyl, ethyl,methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,difluoromethoxy, trifluoromethylthio, phenyl or phenoxy,

q preferably represents the numbers 0, 1, 2 or 3, X³ representingidentical or different radicals if q represents 2 or 3, and

Y¹ preferably represents an oxygen atom, a CH₂ group or a direct bond.

R¹ furthermore preferably represents a radical of the formula ##STR21##

in which

R¹² preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, fluoroalkyl having 1 to 4 carbon-atoms and 1 to 5 fluorineatoms, cycloalkyl having 3 to 6 carbon atoms which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methyl and/orethyl, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkylmoiety and 1 to 3 carbon atoms in the alkyl moiety, phenyl which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/orbromine, or benzyl which is optionally monosubstituted to trisubstitutedby identical or different substituents from the series consisting offluorine, chlorine and/or bromine,

X⁴ preferably represents fluorine, chlorine, bromine, nitro, methyl,ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl which is optionally monosubstituted or disubstituted by identicalor different substituents from the series consisting of fluorine,chlorine, bromine and/or methyl, or phenoxy which is optionallymonosubstituted or disubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine and/or methyl,

r preferably represents the numbers 0, 1, 2 or 3, X⁴ representingidentical or different radicals if r represents 2 or 3, and

Y² preferably represents an oxygen atom or a CH₂ group.

R¹ furthermore preferably represents a radical of the formula ##STR22##

in which

A preferably represents alkanediyl having 2 or 3 carbon atoms which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromine,methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl and/ortert-butyl,

X⁵ preferably represents fluorine, chlorine, bromine, methyl, ethyl,methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, difluoromethoxy, phenyl which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine and/or methyl, and/orphenoxy which is optionally monosubstituted to trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine and/or methyl, and

s preferably represents the numbers 0, 1, 2 or 3, X⁵ representingidentical or different radicals if s represents 2 or 3.

R¹ furthermore preferably represents a radical of the formula ##STR23##

in which

R¹³ preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,fluoroalkoxyalkyl having 1 to 3 carbon atoms and 1 to 5 fluorine atomsin the fluoroalkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety,cycloalkyl having 3 to 6 carbon atoms which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methyl and/orethyl, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkylmoiety and 1 to 3 carbon atoms in the alkyl moiety, phenyl which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/orbromine, or phenylalkyl having 1 or 2 carbon atoms in the alkyl moietywhich is optionally monosubstituted to trisubstituted by identical ordifferent substituents from the series consisting of fluorine, chlorineand/or bromine,

X⁶ preferably represents fluorine, chlorine, bromine, methyl, ethyl;tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromineand/or methyl, or phenoxy which is optionally monosubstituted ordisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine and/or methyl, and

t preferably represents the numbers 0, 1, 2 or 3, X⁶ representingidentical or different radicals if t represents 2 or 3.

R¹ further-more preferably represents a radical of the formula ##STR24##

in which

R¹⁴ preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorineatoms, cycloalkyl having 3 to 6 carbon atoms which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methyl and/orethyl, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkylmoiety and 1 to 3 carbon atoms in the alkyl moiety, phenyl which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/orbromine, or benzyl which is optionally monosubstituted to trisubstitutedby identical or different substituents from the series consisting offluorine, chlorine and/or bromine,

X⁷ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromineand/or methyl, or phenoxy which is optionally monosubstituted ordisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine and/or methyl,

u preferably represents the numbers 0, 1, 2 or 3, X⁷ representingidentical or different radicals if u represents 2 or 3, and

Y³ preferably represents an oxygen atom or a CH₃ group.

Moreover, R¹ also preferably represents a radical of the formula##STR25##

in which

R¹⁵ preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5halogen atoms, phenyl which is optionally monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkylhaving 1 or 2 carbon atoms having 1 to 5 halogen atoms, alkoxy having 1to 4 carbon atoms and/or halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 halogen atoms, or represents phenylalkyl having 1 to 4 carbon atomsin the alkyl moiety which is optionally monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkylhaving 1 or 2 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to4 carbon atoms and/or halogenoalkoxy having 1 or 2 carbon atoms and 1 to5 halogen atoms,

X⁸ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromineand/or methyl, or phenoxy which is optionally monosubstituted ordisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine and/or methyl, and

v preferably represents the numbers 0, 1, 2 or 3, X⁸ representingidentical or different radicals if v represents 2 or 3.

R especially preferably represents hydrogen, methyl or ethyl.

R¹ especially preferably represents a radical of the formula ##STR26##

in which

R² especially preferably represents straight-chain or branched alkylhaving 1 to 4 carbon atoms, it being possible for these radicals to bemonosubstituted to tetrasubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, alkoximino having 1 or 2 carbonatoms in the alkoxy moiety, cyclopropyl, cyclobutyl, cyclopentyl and/orcyclohexyl, or

represents straight-chain or branched alkenyl having 2 to 5 carbonatoms, it being possible for each of these radicals to bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methoxy,ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl, cyclopentyl and/orcyclohexyl, or

represents cycloalkyl having 3 to 6 carbon atoms, it being possible foreach of these radicals to be monosubstituted to trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, cyano, methyl, ethyl, propyl, isopropyland/or tert-butyl, or

represents phenylalkyl having 1 to 4 carbon atoms in the straight-chainor branched alkyl moiety, it being possible for the phenyl moiety to bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methyl,ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methyoximinoethyl, nitro and/orcyano, or

represents phenylalkenyl having 2 to 4 carbon atoms in the alkenylmoiety, it being possible for the phenyl moiety to be monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl,methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy,chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and/or cyano, or

represents phenoxyalkyl having 1 to 4 carbon atoms in the straight-chainor branched oxyalkyl moiety, it being possible for the phenyl moiety tobe monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and/orcyano, or

represents phenyl which can be monosubstituted to trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and/or cyano, or

represents pyrazolyl, imidazolyl, 1,2,4-triazolyl, pyrrolyl, furanyl,thienyl, thiazolyl, oxazolyl, pyridinyl, pyrimidinyl, triazinyl,quinolinyl, isoquinolinyl, quinazolinyl, indolyl, benzothienyl,benzofuranyl, benzothiazolyl or benzimidazolyl, it being possible foreach of these radicals to be monosubstituted to trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, chlorodifluoromethylthio, hydroxymethyl,hydroxyethyl, hydroxyalkinyl having 4 to 6 carbon atoms,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and/or cyano, formyl, dimethoxymethyl, acetyl and/or propionyl,and

R³ especially preferably represents straight-chain or branched alkylhaving 1 to 4 carbon atoms, it being possible for these radicals to bemonosubstituted to tetrasubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, alkoximino having 1 or 2 carbonatoms in the alkoxy moiety, cyclopropyl, cyclobutyl, cyclopentyl and/orcyclohexyl, or

represents straight-chain or branched alkenyl having 2 to 5 carbonatoms, it being possible for each of these radicals to bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methoxy,ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl, cyclopentyl and/orcyclohexyl, or

represents cycloalkyl having 3 to 6 carbon atoms, it being possible foreach of these radicals to be monosubstituted to trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, cyano, methyl, ethyl, propyl, isopropyland/or tert-butyl, or

represents phenylalkyl having 1 to 4 carbon atoms in the straight-chainor branched alkyl moiety, it being possible for the phenyl moiety to bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methyl,ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and/orcyano, or

represents phenylalkenyl having 2 to 4 carbon atoms in the alkenylmoiety, it being possible for the phenyl moiety to be monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl,methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy,chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and/or cyano, or

represents phenoxyalkyl having 1 to 4 carbon atoms in the straight-chainor branched oxyalkyl moiety, it being possible for the phenyl moiety tobe monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and/orcyano, or

represents phenyl which can be monosubstituted to trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and/or cyano, or

represents pyrazolyl, imidazolyl, 1,2,4-triazolyl, pyrrolyl, furanyl,thienyl, thiazolyl, oxazolyl, pyridinyl, pyrimidinyl, triazinyl,quinolinyl, isoquinolinyl, quinazolinyl, indolyl, benzothienyl,benzofuranyl, benzothiazolyl or benzimidazolyl, it being possible foreach of these radicals to be monosubstituted to be trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, chlorodifluoromethylthio, hydroxymethyl,hydroxyethyl, hydroxyalkinyl having 4 to 6 carbon atoms,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and/or cyano, formyl, dimethoxymethyl, acetyl and/or propionyl.

R¹ furthermore especially preferably represents a radical of the formula##STR27##

in which

R⁴ especially preferably represents methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, iso-butyl, tert-butyl, fluoro-tert-butyl,difluoro-tert-butyl, cycloalkyl having 3 to 6 carbon atoms which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/orbromine, or represents naphthyl, or represents phenyl which can bemonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, nitro,phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy,trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl,trifluoromethoxy, difluoromethoxy and/or trifluoromethylthio, and

R⁵ especially preferably represents phenyl which can be monosubstitutedto trisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine, methyl, ethyl, isopropyl,tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, difluorochlormethyl, trifluoromethoxy, difluoromethoxyand/or trifluoromethylthio.

R¹ furthermore especially preferably represents a radical of the formula##STR28##

in which

R⁶ especially preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

R⁷ especially preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

X¹ especially preferably represents fluorine, chlorine, bromine, methyl,ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl,methoxy, ethoxy, phenyl, phenoxy, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy or trifluoromethylthio, and

m also especially preferably represents the numbers 0, 1 or 2,

it being possible for X¹ to represent identical or different radicals ifm represents 2.

R¹ furthermore especially preferably represents a radical of the formula##STR29##

in which

R⁸ especially preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

R⁹ especially preferably represents hydrogen, methyl, n-propyl,isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl, X²especially preferably represents fluorine, chlorine, bromine, cyano,nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl,sec-butyl, tert-butyl, methoxy, ethoxy, trifluoromethyl,trichloromethyl, difluoromethyl, trichloromethoxy, trifluoromethoxy,difluoromethoxy, difluorochloromethoxy or phenyl,

n also especially preferably represents the numbers 0 or 1 and p alsoespecially preferably represents the numbers 0, 1 or 2,

it being possible for X² to represent identical or different radicals ifp represents 2.

R¹ furthermore especially preferably represents a radical of the formula##STR30##

in which

R¹⁰ especially preferably represents methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, iso-butyl, tert-butyl, halogenoalkyl having 1 to 4carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms,cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, methyl and/orethyl, and represents phenyl, benzyl or phenethyl, it being possible foreach of the three last-mentioned radicals to be monosubstituted totrisubstituted in the phenyl moiety by identical or differentsubstituents from the series consisting of fluorine, chlorine, bromine,methyl, ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl and/orphenoxy.

R¹ furthermore especially preferably represents a radical of the formula##STR31##

in which

R¹¹ especially preferably represents hydrogen, straight-chain orbranched alkyl having 1 to 6 carbon atoms, or cyclopropyl, cyclopentylor cyclohexyl, each of which is optionally monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine, methyl and/or ethyl,

X³ especially preferably represents fluorine, chlorine, bromine, methyl,methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,difluoromethoxy, trifluoromethylthio, phenyl or phenoxy,

q also especially preferably represents the numbers 0, 1, 2 or 3, X³representing identical or different radicals if q represents 2 or 3 and

Y¹ also especially preferably represents an oxygen atom, a CH₂ group ora direct bond.

R¹ furthermore especially preferably represents a radical of the formula##STR32##

in which

R¹² especially preferably represents methyl, isopropyl, tert-butyl,fluoro-tert-butyl, difluoro-tert-butyl, or represents cyclopropyl,cyclopentyl or cyclohexyl, each of which is optionally monosubstitutedto trisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine and/or methyl, or represents cycloalkylhaving 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbonatoms in the alkyl moiety, phenyl which is optionally monosubstituted ordisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine and/or bromine, or benzyl which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/orbromine,

X⁴ especially preferably represents fluorine, chlorine, bromine, nitro,methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy,

r also especially preferably represents the numbers 0, 1, 2 or 3, X⁴representing identical or different radicals if r represents 2 or 3 and

Y² also especially represents an oxygen atom or a CH₂ group.

R¹ furthermore especially preferably represents a radical of the formula##STR33##

in which

A especially preferably represents alkanediyl having 2 or 3 carbon atomswhich is optionally monosubstituted to trisubstituted by identical ordifferent substituents from the series consisting of fluorine, chlorine,bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl,sec-butyl, and/or tert-butyl,

X⁵ especially preferably represents fluorine, chlorine, bromine, methyl,ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, difluoromethoxy, phenyl which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/ormethyl, and/or phenoxy which is optionally monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine and/or methyl and

s also especially preferably represents the numbers 0, 1, 2 or 3, X⁵representing identical or different radicals if s represents 2 or 3.

R¹ furthermore preferably represents a radical of the formula ##STR34##

in which

R¹³ especially preferably represents methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl, halogenoalkyl having 1 to 4carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,fluoroalkoxyalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine atomsin the fluoroalkoxy moiety and 1 or 2 carbon atoms in the alkyl moiety,or represents cyclopropyl, cyclopentyl or cyclohexyl, each of which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/ormethyl, or represents cycloalkylalkyl having 3 to 6 carbon atoms in thecycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, orrepresents phenyl which is optionally monosubstituted or disubtituted byidentical or different substituents from the series consisting offluorine, chlorine and/or bromine, or represents benzyl which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series consisting of fluorine, chlorine and/orbromine,

X⁶ especially preferably represents fluorine, chlorine, bromine, methyl,ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy and

t also especially preferably represents the numbers 0, 1, 2 or 3, X⁶representing identical or different radicals if t represents 2 or 3.

R¹ furthermore especially preferably represents a radical of the formula##STR35##

in which

R¹⁴ especially preferably represents methyl, isopropyl, tert-butyl,fluoro-tert-butyl, difluoro-tert-butyl, or represents cyclopropyl,cyclopentyl or cyclohexyl, each of which is optionally monosubstitutedto trisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine and/or methyl, or representscycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 or 2 carbon atoms in the alkyl moiety, phenyl which is optionallymonosubstituted or disubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine and/or bromine, orbenzyl which is optionally monosubstituted or disubstituted by identicalor different substituents from the series consisting of fluorine,chlorine and/or bromine,

X⁷ especially preferably represents fluorine, chlorine, bromine, methyl,ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy,

Y³ also especially preferably represents an oxygen atom or a CH₂ group,and

u also especially preferably represents the numbers 0, 1, 2 or 3, X⁷representing identical or different radicals if u represents 2 or 3.

Moreover, R¹ also preferably represents a radical of the formula##STR36##

in which

R¹⁵ especially preferably represents methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, isobutyl, tert-butyl, fluoro-tert-butyl,difluoro-tert-butyl, phenyl which is optionally monosubstituted ordisubstituted by identical or different substituents from the seriesconsisting of fluorine, chlorine, methyl, ethyl, trifluoromethyl,trichloromethyl, methoxy, ethoxy, trifluoromethoxy and/ordifluoromethoxy, or represents phenylalkyl having 1 or 2 carbon atoms inthe alkyl moiety which is optionally monosubstituted or disubstituted inthe phenyl moiety by identical or different substituents from the seriesconsisting of fluorine, chlorine, bromine, methyl, ethyl, trifluomethyl,trichloromethyl, methoxy, ethoxy, trifluoromethoxy and/ordifluoromethoxy,

X⁸ especially preferably represents fluorine, chlorine, bromine, methyl,ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy, and

v also especially preferably represents the numbers 0, 1, 2 or 3, X⁸representing identical or different radicals if v represents 2 or 3.

Other preferred compounds according to the invention are adducts ofacids and those mercapto-imidazolyl derivatives of the formula (I) inwhich R and R¹ have those meanings which have been mentioned as beingespecially preferred for these substituents.

The acids which can be subjected to the addition reaction preferablyinclude hydrohalic acids such as, for example hydrochloric acid andhydrobromic acid, in particular hydrochloric acid, furthermorephosphoric acid, nitric acid, mono- and bifunctional carboxylic acidsand hydroxycarboxylic acids such as, for example, acetic acid, maleicacid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylicacid, sorbic acid and lactic acid, and also sulphonic acids such as, forexample, p-toluenesulphonic acid and 1,5-naphthalenedisulphonic acid,and also saccharin and thiosaccharin.

Other preferred compounds according to the invention are adducts ofsalts of metals of main groups II to IV and sub-groups I and II and IVto VIII of the Periodic Table and those mercapto-imidazolyl derivativesof the formula (I) in which R and R¹ have those meanings which have beenmentioned as being preferred for these substituents.

Salts of copper, zinc, manganese, magnesium, tin, iron and of nickel areespecially preferred in this context. Suitable anions of these salts arethose which are derived from those acids which lead to physiologicallyacceptable adducts. Especially preferred acids of this type are, in thiscontext, the hydrohalic acids such as, for example, hydrochloric acidand hydrobromic acid, furthermore phosphoric acid, nitric acid andsulphuric acid.

The mercapto-imidazolyl derivatives of the formula (I) according to theinvention in which R represents hydrogen can exist in the "mercapto"form, of the formula ##STR37## or in the tautomeric "thiono" form, ofthe formula ##STR38##

For the sake of simplicity, only the "mercapto" form is shown in eachcase.

Examples of substances according to the invention which may be mentionedare the mercapto-imidazolyl derivatives shown in the tables whichfollow.

                  TABLE 1                                                         ______________________________________                                                                      (Ic)                                                                            #STR39##                                         -                                                                          R.sup.2             R.sup.3      R                                            ______________________________________                                                                           #STR40##                                                                    --C(CH.sub.3).sub.3 --CH.sub.3                  -                                                                                                             --C(CH.sub.3).sub.3 H                         -                                                                                                             --C(CH.sub.3).sub.3 --CH.sub.3                                                -                                                                             --C(CH.sub.3).sub.3 H                         -                                                                                                             --C(CH.sub.3).sub.3 --CH.sub.3                                                -                                                                             --C(CH.sub.3).sub.3 H                         -                                                                                                             #STR46##                                                                      --CH.sub.3                                    -                                                                                                             #STR48##                                                                      H TR49##                                      -                                                                                                             --C.sub.4 H.sub.9 -n --CH.sub.3                                               -                                                                             --C.sub.4 H.sub.9 -n H                        -                                                                                                             #STR52##                                                                      --CH.sub.3                                    -                                                                                                             #STR54##                                                                      H TR55##                                      -                                                                                                             --C(CH.sub.3).sub.3 --CH.sub.3                                                -                                                                             --C(CH.sub.3).sub.3 H                         - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 -- --C(CH.sub.3).sub.3 --CH.sub.3                                        Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                         --C(CH.sub.3).sub.3 H                           - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                        --CH.sub.3                                    - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                        H TR59##                                      - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                        --CH.sub.3                                    - Cl.sub.2 CH--CCl.sub.2 --CH.sub.2 --                                                                        H TR61##                                      -                                                                                                             --C(CH.sub.3).sub.3 --CH.sub.3                                                -                                                                             --C(CH.sub.3).sub.3 H                         -                                                                                                             #STR64##                                                                      --CH.sub.3                                    -                                                                                                             #STR66##                                                                      H TR67##                                      -                                                                                                             #STR68##                                                                      H TR69##                                      -                                                                                                             #STR70##                                                                      H TR71##                                      -                                                                                                             #STR72##                                                                      --CH.sub.3                                    - Cl.sub.2 CH--CCl.sub.2 --                                                                                   --CH.sub.3                                    -                                                                                                             --C(CH.sub.3).sub.3 --CH.sub.3                                                -                                                                             --C(CH.sub.3).sub.3 --CH.sub.3                                                - Cl.sub.2 C═CCl--CH.sub.2 --                                             H TR77##                                      - Cl.sub.2 C═CCl--CH.sub.2 --                                                                             CH.sub.3                                   ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                                                     (Id)                                                                            #STR79##                                          -                                                                          R.sup.4             R.sup.5      R                                            ______________________________________                                                                           #STR80##                                                                      #STR81##                                                                    --CH.sub.3                                      -                                                                                                             #STR82##                                                                      --CH.sub.3                                    -                                                                                                             #STR84##                                                                      --CH.sub.3                                    -                                                                                                             #STR86##                                                                      --CH.sub.3                                    -                                                                                                             #STR88##                                                                      --CH.sub.3                                    -                                                                                                             #STR90##                                                                      --CH.sub.3                                    -                                                                                                             #STR92##                                                                      --CH.sub.3                                    -                                                                                                             #STR94##                                                                      --CH.sub.3                                    -                                                                                                             #STR96##                                                                      --CH.sub.3                                    -                                                                                                             #STR98##                                                                      --CH.sub.3                                    -                                                                                                             #STR100##                                                                     --CH.sub.3                                    -                                                                                                             #STR102##                                                                     --CH.sub.3                                    -                                                                                                             #STR104##                                                                     --CH.sub.3                                    -                                                                                                             #STR106##                                                                     --CH.sub.3                                    -                                                                                                             #STR108##                                                                     --CH.sub.3                                    -                                                                                                             #STR110##                                                                     --CH.sub.3                                    -                                                                                                             #STR112##                                                                     --CH.sub.3                                    -                                                                                                             #STR114##                                                                     --CH.sub.3                                    -                                                                                                             #STR116##                                                                     --CH.sub.3                                    -                                                                                                             #STR118##                                                                     --CH.sub.3                                    -                                                                                                             #STR120##                                                                     --CH.sub.3                                    -                                                                                                             #STR122##                                                                     --CH.sub.3                                    -                                                                                                             #STR124##                                                                     --CH.sub.3                                    -                                                                                                             #STR126##                                                                     --CH.sub.3                                    -                                                                                                             #STR128##                                                                     --CH.sub.3                                    -                                                                                                             #STR130##                                                                     --CH.sub.3                                    -                                                                                                             #STR132##                                                                     --CH.sub.3                                    -                                                                                                             #STR134##                                                                     --CH.sub.3                                    -                                                                                                             #STR136##                                                                     --CH.sub.3                                    -                                                                                                             #STR138##                                                                     --CH.sub.3                                    -                                                                                                             #STR140##                                                                     --CH.sub.3                                    -                                                                                                             #STR142##                                                                     --CH.sub.3                                    -                                                                                                             #STR144##                                                                     --CH.sub.3                                    -                                                                                                             #STR146##                                                                     --CH.sub.3                                    -                                                                                                             #STR148##                                                                     --CH.sub.3                                    -                                                                                                             #STR150##                                                                     --CH.sub.3                                    -                                                                                                             #STR152##                                                                     --CH.sub.3                                    -                                                                                                             #STR154##                                                                     --CH.sub.3                                    -                                                                                                             #STR156##                                                                     --CH.sub.3                                    -                                                                                                             #STR158##                                                                     --CH.sub.3                                    -                                                                                                             #STR160##                                                                     --CH.sub.3                                    -                                                                                                             #STR162##                                                                     --CH.sub.3                                    -                                                                                                             #STR164##                                                                     --CH.sub.3                                    -                                                                                                             #STR166##                                                                     --CH.sub.3                                    -                                                                                                             #STR168##                                                                     --CH.sub.3                                    -                                                                                                             #STR170##                                                                     --CH.sub.3                                    -                                                                                                             #STR172##                                                                     --CH.sub.3                                    -                                                                                                             #STR174##                                                                     --CH.sub.3                                    - --CH.sub.3                                                                                                  --CH.sub.3                                    - --CH.sub.3                                                                                                  --CH.sub.3                                    - --CH.sub.3                                                                                                  --CH.sub.3                                    - --C(CH.sub.3).sub.3                                                                                         --CH.sub.3                                    -                                                                                                             #STR180##                                                                     --CH.sub.3                                    -                                                                                                             #STR182##                                                                     H TR183##                                     -                                                                                                             #STR184##                                                                     H TR185##                                     -                                                                                                             #STR186##                                                                     H TR187##                                     -                                                                                                             #STR188##                                                                     H TR189##                                     -                                                                                                             #STR190##                                                                     H TR191##                                     -                                                                                                             #STR192##                                                                     H TR193##                                     -                                                                                                             #STR194##                                                                     H TR195##                                     -                                                                                                             #STR196##                                                                     H TR197##                                     -                                                                                                             #STR198##                                                                     H TR199##                                     -                                                                                                             #STR200##                                                                     H TR201##                                     -                                                                                                             #STR202##                                                                     H TR203##                                     -                                                                                                             #STR204##                                                                     H TR205##                                     -                                                                                                             #STR206##                                                                     H TR207##                                     -                                                                                                             #STR208##                                                                     H TR209##                                     -                                                                                                             #STR210##                                                                     H TR211##                                     -                                                                                                             #STR212##                                                                     H TR213##                                     -                                                                                                             #STR214##                                                                     H TR215##                                     -                                                                                                             #STR216##                                                                     H TR217##                                     -                                                                                                             #STR218##                                                                     H TR219##                                     -                                                                                                             #STR220##                                                                     H TR221##                                     -                                                                                                             #STR222##                                                                     H TR223##                                     -                                                                                                             #STR224##                                                                     H TR225##                                     -                                                                                                             #STR226##                                                                     H TR227##                                     -                                                                                                             #STR228##                                                                     H TR229##                                     -                                                                                                             #STR230##                                                                     H TR231##                                     -                                                                                                             #STR232##                                                                     H TR233##                                     -                                                                                                             #STR234##                                                                     H TR235##                                     -                                                                                                             #STR236##                                                                     H TR237##                                     -                                                                                                             #STR238##                                                                     H TR239##                                     -                                                                                                             #STR240##                                                                     H TR241##                                     -                                                                                                             #STR242##                                                                     H TR243##                                     -                                                                                                             #STR244##                                                                     H TR245##                                     -                                                                                                             #STR246##                                                                     H TR247##                                     -                                                                                                             #STR248##                                                                     H TR249##                                     -                                                                                                             #STR250##                                                                     H TR251##                                     -                                                                                                             #STR252##                                                                     H TR253##                                     -                                                                                                             #STR254##                                                                     H TR255##                                     -                                                                                                             #STR256##                                                                     H TR257##                                     -                                                                                                             #STR258##                                                                     H TR259##                                     -                                                                                                             #STR260##                                                                     H TR261##                                     -                                                                                                             #STR262##                                                                     H TR263##                                     -                                                                                                             #STR264##                                                                     H TR265##                                     -                                                                                                             #STR266##                                                                     H TR267##                                     -                                                                                                             #STR268##                                                                     H TR269##                                     -                                                                                                             #STR270##                                                                     H TR271##                                     -                                                                                                             #STR272##                                                                     H TR273##                                     -                                                                                                             #STR274##                                                                     H TR275##                                     -                                                                                                             #STR276##                                                                     H TR277##                                     -                                                                                                             #STR278##                                                                     H TR279##                                     - --CH.sub.3                                                                                                  H TR280##                                     - --CH.sub.3                                                                                                  H TR281##                                     - --CH.sub.3                                                                                                  H TR282##                                     - --C(CH.sub.3).sub.3                                                                                         H TR283##                                     -                                                                                                             #STR284##                                                                     HSTR285##                                  ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                                                      (Ie)                                                                            #STR286##                                        -                                                                          R.sup.6    R.sup.7   R         X.sup.1.sub.m                                  ______________________________________                                        --CH.sub.3 --CH.sub.3                                                                              --CH.sub.3                                                                              4-Br                                             --CH.sub.3 --CH.sub.3 --CH.sub.3 4-F                                          --CH.sub.3 --CH.sub.3 --CH.sub.3 2,4-Cl.sub.2                                 --CH.sub.3 H --CH.sub.3 4-Cl                                                  --CH.sub.3 --CH.sub.3 --CH.sub.3 --                                           --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CH.sub.3                                   --CH.sub.3 --CH.sub.3 --CH.sub.3 2-F, 4-Cl                                    --C.sub.2 H.sub.5 H --CH.sub.3 4-Cl                                           --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl                           --C.sub.3 H.sub.7 -n H --CH.sub.3 4-Cl                                        --C.sub.2 H.sub.5 H --CH.sub.3 2,4-Cl.sub.2                                   --C.sub.2 H.sub.5 H --CH.sub.3 4-F                                            --C.sub.2 H.sub.5 H --CH.sub.3 4-Br                                            - --C.sub.2 H.sub.5 H --CH.sub.3                                                                            #STR287##                                       - --C.sub.2 H.sub.5 H --CH.sub.3 4-C.sub.4 H.sub.9 -t                        --C.sub.3 H.sub.7 -i H --CH.sub.3 4-Cl                                        --C.sub.5 H.sub.11 -n H --CH.sub.3 4-Cl                                        - --CH.sub.3 --CH.sub.3 --CH.sub.3                                                                          #STR288##                                       - --CH.sub.3 --CH.sub.3 --CH.sub.3 4-C.sub.4 H.sub.9 -t                      --C.sub.4 H.sub.9 -n H --CH.sub.3 4-Cl                                        --C.sub.4 H.sub.9 -i H --CH.sub.3 4-Cl                                        --CH.sub.3 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl                                  --CH.sub.3 --CH.sub.3 H 4-Cl                                                  --CH.sub.3 --CH.sub.3 H 4-Br                                                  --CH.sub.3 --CH.sub.3 H 4-F                                                   --CH.sub.3 --CH.sub.3 H 2,4-Cl.sub.2                                          --CH.sub.3 H H 4-Cl                                                           --CH.sub.3 --CH.sub.3 H --                                                    --CH.sub.3 --CH.sub.3 H 4-CH.sub.3                                            --CH.sub.3 --CH.sub.3 H 2-F, 4-Cl                                             --C.sub.2 H.sub.5 H H 4-Cl                                                    --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 H 4-Cl                                    --C.sub.3 H.sub.7 -n H H 4-Cl                                                 --C.sub.2 H.sub.5 H H 2,4-Cl.sub.2                                            --C.sub.2 H.sub.5 H H 4-F                                                     --C.sub.2 H.sub.5 H H 4-Br                                                     - --C.sub.2 H.sub.5 H H                                                                                     #STR289##                                       - --C.sub.2 H.sub.5 H H 4-C.sub.4 H.sub.9 -t                                 --C.sub.3 H.sub.7 -i H H 4-Cl                                                 --C.sub.5 H.sub.11 -n H H 4-Cl                                                 - --CH.sub.3 --CH.sub.3 H                                                                                   #STR290##                                       - --CH.sub.3 --CH.sub.3 H 4-C.sub.4 H.sub.9 -t                               --C.sub.4 H.sub.9 -n H H 4-Cl                                                 --C.sub.4 H.sub.9 -i H H 4-Cl                                                 --CH.sub.3 --C.sub.2 H.sub.5 H 4-Cl                                           --CH.sub.3 --CH.sub.3 --CH.sub.3 2-Cl                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 2,3-Cl.sub.2                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CF.sub.3                                   --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCF.sub.3                                  --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Cl                                       ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                                       (If)                                                                            #STR291##                                       -                                                                          R.sup.8   R.sup.9   R         X.sup.2.sub.p                                                                          n                                      ______________________________________                                        --CH.sub.3                                                                              --CH.sub.3                                                                              --CH.sub.3                                                                              4-Br     0                                        --CH.sub.3 --CH.sub.3 --CH.sub.3 4-F 0                                        --CH.sub.3 --CH.sub.3 --CH.sub.3 2,4-Cl.sub.2 0                               --CH.sub.3 H --CH.sub.3 4-Cl 0                                                --CH.sub.3 --CH.sub.3 --CH.sub.3 -- 0                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CH.sub.3 0                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-F, 4-Cl 0                                  --C.sub.2 H.sub.5 H --CH.sub.3 4-Cl 0                                         --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 0                         --C.sub.3 H.sub.7 -n H --CH.sub.3 4-Cl 0                                      --C.sub.2 H.sub.5 H --CH.sub.3 2,4-Cl.sub.2 0                                 --C.sub.2 H.sub.5 H --CH.sub.3 4-F 0                                          --C.sub.2 H.sub.5 H --CH.sub.3 4-Br 0                                         --C.sub.2 H.sub.5 H --CH.sub.3 4-NO.sub.2 0                                   --C.sub.2 H.sub.5 H --CH.sub.3 4-C.sub.4 H.sub.9 -t 0                         --C.sub.3 H.sub.7 -i H --CH.sub.3 4-Cl 0                                      --C.sub.5 H.sub.11 -n H --CH.sub.3 4-Cl 0                                     --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CN 0                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-C.sub.4 H.sub.9 -t 0                       --C.sub.4 H.sub.9 -n H --CH.sub.3 4-Cl 0                                      --C.sub.4 H.sub.9 -i H --CH.sub.3 4-Cl 0                                      --CH.sub.3 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 0                                --CH.sub.3 --CH.sub.3 H 4-Cl 0                                                --CH.sub.3 --CH.sub.3 H 4-Br 0                                                --CH.sub.3 --CH.sub.3 H 4-F 0                                                 --CH.sub.3 --CH.sub.3 H 2,4-Cl.sub.2 0                                        --CH.sub.3 H H 4-Cl 0                                                         --CH.sub.3 --CH.sub.3 H -- 0                                                  --CH.sub.3 --CH.sub.3 H 4-CH.sub.3 0                                          --CH.sub.3 --CH.sub.3 H 2-F, 4-Cl 0                                           --C.sub.2 H.sub.5 H H 4-Cl 0                                                  --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 H 4-Cl 0                                  --C.sub.3 H.sub.7 -n H H 4-Cl 0                                               --C.sub.2 H.sub.5 H H 2,4-Cl.sub.2 0                                          --C.sub.2 H.sub.5 H H 4-F 0                                                   --C.sub.2 H.sub.5 H H 4-Br 0                                                  --C.sub.2 H.sub.5 H H 4-NO.sub.2 0                                            --C.sub.2 H.sub.5 H H 4-C.sub.4 H.sub.9 -t 0                                  --C.sub.3 H.sub.7 -i H H 4-Cl 0                                               --C.sub.5 H.sub.11 -n H H 4-Cl 0                                              --CH.sub.3 --CH.sub.3 H 4-CN 0                                                --CH.sub.3 --CH.sub.3 H 4-C.sub.4 H.sub.9 -t 0                                --C.sub.4 H.sub.9 -n H H 4-Cl 0                                               --C.sub.4 H.sub.9 -i H H 4-Cl 0                                               --CH.sub.3 --C.sub.2 H.sub.5 H 4-Cl 0                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCH.sub.3 0                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCH.sub.3 0                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-CF.sub.3 0                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CF.sub.3 0                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCF.sub.3 0                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCHF.sub.2 0                               --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCF.sub.3 0                                --CH.sub.3 --CH.sub.3 H 4-OCH.sub.3 0                                         --CH.sub.3 --CH.sub.3 H 2-OCH.sub.3 0                                         --CH.sub.3 --CH.sub.3 H 2-CF.sub.3 0                                          --CH.sub.3 --CH.sub.3 H 4-CF.sub.3 0                                          --CH.sub.3 --CH.sub.3 H 2-OCF.sub.3 0                                         --CH.sub.3 --CH.sub.3 H 2-OCHF.sub.2 0                                        --CH.sub.3 --CH.sub.3 H 4-OCF.sub.3 0                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Br 1                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-F 1                                        --CH.sub.3 --CH.sub.3 --CH.sub.3 2,4-Cl.sub.2 1                               --CH.sub.3 H --CH.sub.3 4-Cl 1                                                --CH.sub.3 --CH.sub.3 --CH.sub.3 -- 1                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CH.sub.3 1                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-F, 4-Cl 1                                  --C.sub.2 H.sub.5 H --CH.sub.3 4-Cl 1                                         --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 1                         --C.sub.3 H.sub.7 -n H --CH.sub.3 4-Cl 1                                      --C.sub.2 H.sub.5 H --CH.sub.3 2,4-Cl.sub.2 1                                 --C.sub.2 H.sub.5 H --CH.sub.3 4-F 1                                          --C.sub.2 H.sub.5 H --CH.sub.3 4-Br 1                                         --C.sub.2 H.sub.5 H --CH.sub.3 4-NO.sub.2 1                                   --C.sub.2 H.sub.5 H --CH.sub.3 4-C.sub.4 H.sub.9 -t 1                         --C.sub.3 H.sub.7 -i H --CH.sub.3 4-Cl 1                                      --C.sub.5 H.sub.11 -n H --CH.sub.3 4-Cl 1                                     --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CN 1                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-C.sub.4 H.sub.9 -t 1                       --C.sub.4 H.sub.9 -n H --CH.sub.3 4-Cl 1                                      --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Cl 1                                       --CH.sub.3 --CH.sub.3 H 4-Cl 1                                                --C.sub.4 H.sub.9 -i H --CH.sub.3 4-Cl 1                                      --CH.sub.3 --C.sub.2 H.sub.5 --CH.sub.3 4-Cl 1                                --CH.sub.3 --CH.sub.3 H 4-Cl 1                                                --CH.sub.3 --CH.sub.3 H 4-Br 1                                                --CH.sub.3 --CH.sub.3 H 4-F 1                                                 --CH.sub.3 --CH.sub.3 H 2,4-Cl.sub.2 1                                        --CH.sub.3 H H 4-Cl 1                                                         --CH.sub.3 --CH.sub.3 H -- 1                                                  --CH.sub.3 --CH.sub.3 H 4-CH.sub.3 1                                          --CH.sub.3 --CH.sub.3 H 2-F, 4-Cl 1                                           --C.sub.2 H.sub.5 H H 4-Cl 1                                                  --C.sub.2 H.sub.5 --C.sub.2 H.sub.5 H 4-Cl 1                                  --C.sub.3 H.sub.7 -n H H 4-Cl 1                                               --C.sub.2 H.sub.5 H H 2,4-Cl.sub.2 1                                          --C.sub.2 H.sub.5 H H 4-F 1                                                   --C.sub.2 H.sub.5 H H 4-Br 1                                                  --C.sub.2 H.sub.5 H H 4-NO.sub.2 1                                            --C.sub.2 H.sub.5 H H 4-C.sub.4 H.sub.9 -t 1                                  --C.sub.3 H.sub.7 -i H H 4-Cl 1                                               --C.sub.5 H.sub.11 -n H H 4-Cl 1                                              --CH.sub.3 --CH.sub.3 H 4-CN 1                                                --CH.sub.3 --CH.sub.3 H 4-C.sub.4 H.sub.9 -t 1                                --C.sub.4 H.sub.9 -n H H 4-Cl 1                                               --C.sub.4 H.sub.9 -i H H 4-Cl 1                                               --CH.sub.3 --C.sub.2 H.sub.5 H 4-Cl 1                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCH.sub.3 1                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCH.sub.3 1                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-CF.sub.3 1                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 4-CF.sub.3 1                                 --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCF.sub.3 1                                --CH.sub.3 --CH.sub.3 --CH.sub.3 2-OCHF.sub.2 1                               --CH.sub.3 --CH.sub.3 --CH.sub.3 4-OCF.sub.3 1                                --CH.sub.3 --CH.sub.3 H 4-OCH.sub.3 1                                         --CH.sub.3 --CH.sub.3 H 2-OCH.sub.3 1                                         --CH.sub.3 --CH.sub.3 H 2-CF.sub.3 1                                          --CH.sub.3 --CH.sub.3 H 4-CF.sub.3 1                                          --CH.sub.3 --CH.sub.3 H 2-OCF.sub.3 1                                         --CH.sub.3 --CH.sub.3 H 2-OCHF.sub.2 1                                        --CH.sub.3 --CH.sub.3 H 4-OCF.sub.3 1                                         --CH.sub.3 --CH.sub.3 --CH.sub.3 2-Cl 0                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 2,3-Cl.sub.2 0                               --CH.sub.3 --CH.sub.3 --CH.sub.3 2-Cl 1                                       --CH.sub.3 --CH.sub.3 --CH.sub.3 4-Cl 0                                     ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                                                      (Ig)                                                                            #STR292##                                        -                                                                          R.sup.10                  R                                                   ______________________________________                                                                    #STR293##                                                                   --CH.sub.3                                             -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           - --C.sub.4 H.sub.9 -n --CH.sub.3                                            --C(CH.sub.3).sub.3 --CH.sub.3                                                --CH(CH.sub.3).sub.2 --CH.sub.3                                                -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           - --CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.3                                  -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      --CH.sub.3                                           -                                                                                                      H TR329##                                            -                                                                                                      H TR330##                                            -                                                                                                      H TR331##                                            -                                                                                                      H TR332##                                            -                                                                                                      H TR333##                                            -                                                                                                      H TR334##                                            -                                                                                                      H TR335##                                            -                                                                                                      H TR336##                                            -                                                                                                      H TR337##                                            - --C.sub.4 H.sub.9 -n H                                                     --C(CH.sub.3).sub.3 H                                                         --CH(CH.sub.3).sub.2 H                                                         -                                                                                                      H TR338##                                            -                                                                                                      H TR339##                                            - --CH.sub.2 --CH(CH.sub.3).sub.2 H                                           -                                                                                                      H TR340##                                            -                                                                                                      H TR341##                                            -                                                                                                      H TR342##                                            -                                                                                                      H TR343##                                            -                                                                                                      H TR344##                                            -                                                                                                      H TR345##                                            -                                                                                                      H TR346##                                            -                                                                                                      H TR347##                                            -                                                                                                      H TR348##                                            -                                                                                                      H TR349##                                            -                                                                                                      H TR350##                                            -                                                                                                      H TR351##                                            -                                                                                                      H TR352##                                            -                                                                                                      H TR353##                                            -                                                                                                      H TR354##                                            -                                                                                                      H TR355##                                            -                                                                                                      H TR356##                                            -                                                                                                      H TR357##                                            -                                                                                                      H TR358##                                            -                                                                                                      H TR359##                                            -                                                                                                      H TR360##                                            -                                                                                                      H TR361##                                            -                                                                                                      H TR362##                                            -                                                                                                      H TR363##                                            -                                                                                                      H TR364##                                            -                                                                                                      --CH.sub.3                                           -                                                                                                      HSTR366##                                         ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                                                      (Ih)                                                                            #STR367##                                        -                                                                          X.sup.3.sub.q Y.sup.1  R.sup.11     R                                         ______________________________________                                        4-Cl          CH.sub.2 H            --CH.sub.3                                  4-CF.sub.3 CH.sub.2 H --CH.sub.3                                              4-OCF.sub.3 CH.sub.2 H --CH.sub.3                                             2,4-Cl.sub.2 CH.sub.2 H --CH.sub.3                                            4-CH.sub.3 CH.sub.2 H --CH.sub.3                                              2-Cl CH.sub.2 H --CH.sub.3                                                    2-F CH.sub.2 H --CH.sub.3                                                     4-F CH.sub.2 H --CH.sub.3                                                     2-OCHF.sub.2 CH.sub.2 H --CH.sub.3                                            4-Cl O H --CH.sub.3                                                           4-CF.sub.3 O H --CH.sub.3                                                     4-OCF.sub.3 O H --CH.sub.3                                                    2,4-Cl.sub.2 O H --CH.sub.3                                                   4-CH.sub.3 O H --CH.sub.3                                                     2-Cl O H --CH.sub.3                                                           2-F O H --CH.sub.3                                                            4-F O H --CH.sub.3                                                            2-OCHF.sub.2 O H --CH.sub.3                                                   4-Cl -- H --CH.sub.3                                                          4-CF.sub.3 -- H --CH.sub.3                                                    4-OCF.sub.3 -- H --CH.sub.3                                                   2,4-Cl.sub.2 -- H --CH.sub.3                                                  4-CH.sub.3 -- H --CH.sub.3                                                    2-Cl -- H --CH.sub.3                                                          2-F -- H --CH.sub.3                                                           4-F -- H --CH.sub.3                                                           2-OCHF.sub.2 -- H --CH.sub.3                                                  4-Cl CH.sub.2 --CH.sub.3 --CH.sub.3                                           4-CF.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                                     4-OCF.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                                    2,4-Cl.sub.2 CH.sub.2 --CH.sub.3 --CH.sub.3                                   4-CH.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                                     2-Cl CH.sub.2 --CH.sub.3 --CH.sub.3                                           2-F CH.sub.2 --CH.sub.3 --CH.sub.3                                            4-F CH.sub.2 --CH.sub.3 --CH.sub.3                                            2-OCHF.sub.2 CH.sub.2 --CH.sub.3 --CH.sub.3                                   4-Cl O --CH.sub.3 --CH.sub.3                                                  4-CF.sub.3 O --CH.sub.3 --CH.sub.3                                            2,4-Cl.sub.2 O --CH.sub.3 --CH.sub.3                                          4-OCF.sub.3 O --CH.sub.3 --CH.sub.3                                           2-F O --CH.sub.3 --CH.sub.3                                                   2-OCHF.sub.2 O --CH.sub.3 --CH.sub.3                                          4-Cl -- --CH.sub.3 --CH.sub.3                                                 4-CF.sub.3 -- --CH.sub.3 --CH.sub.3                                           2,4-Cl.sub.2 -- --CH.sub.3 --CH.sub.3                                         4-OCF.sub.3 -- --CH.sub.3 --CH.sub.3                                          2-F -- --CH.sub.3 --CH.sub.3                                                  2-OCHF.sub.2 -- --CH.sub.3 --CH.sub.3                                         4-Cl CH.sub.2 C.sub.4 H.sub.9 -n --CH.sub.3                                   2,4-Cl.sub.2 CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.3                         4-OCF.sub.3 CH.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3                            - 4-Cl CH.sub.2                                                                                                  --CH.sub.3                                 - 4-Cl CH.sub.2                                                                                                  --CH.sub.3                                 - 4-Cl CH.sub.2                                                                                                  --CH.sub.3                                 - 4-Cl CH.sub.2                                                                                                  --CH.sub.3                                 - 2,4,6-Cl.sub.3 CH.sub.2 --CH.sub.3 --CH.sub.3                               -                                                                                                                CH.sub.2 --CH.sub.3 --CH.sub.3                                                -                                                                             CH.sub.2 --CH.sub.3 --CH.sub.3                                                - 4-Cl CH.sub.2 H H                       4-CF.sub.3 CH.sub.2 H H                                                       4-OCF.sub.3 CH.sub.2 H H                                                      2,4-Cl.sub.2 CH.sub.2 H H                                                     4-CH.sub.3 CH.sub.2 H H                                                       2-Cl CH.sub.2 H H                                                             2-F CH.sub.2 H H                                                              4-F CH.sub.2 H H                                                              2-OCHF.sub.2 CH.sub.2 H H                                                     4-Cl O H H                                                                    4-CF.sub.3 O H H                                                              4-OCF.sub.3 O H H                                                             2,4-Cl.sub.2 O H H                                                            4-CH.sub.3 O H H                                                              2-Cl O H H                                                                    2-F O H H                                                                     4-F O H H                                                                     2-OCHF.sub.2 O H H                                                            4-Cl -- H H                                                                   4-CF.sub.3 -- H H                                                             4-OCF.sub.3 -- H H                                                            2,4-Cl.sub.2 -- H H                                                           4-CH.sub.3 -- H H                                                             2-Cl -- H H                                                                   2-F -- H H                                                                    4-F -- H H                                                                    2-OCHF.sub.2 -- H H                                                           4-Cl CH.sub.2 --CH.sub.3 H                                                    4-CF.sub.3 CH.sub.2 --CH.sub.3 H                                              4-OCF.sub.3 CH.sub.2 --CH.sub.3 H                                             2,4-Cl.sub.2 CH.sub.2 --CH.sub.3 H                                            4-CH.sub.3 CH.sub.2 --CH.sub.3 H                                              2-Cl CH.sub.2 --CH.sub.3 H                                                    2-F CH.sub.2 --CH.sub.3 H                                                     4-F CH.sub.2 --CH.sub.3 H                                                     2-OCHF.sub.2 CH.sub.2 --CH.sub.3 H                                            4-Cl O --CH.sub.3 H                                                           4-CF.sub.3 O --CH.sub.3 H                                                     2,4-Cl.sub.2 O --CH.sub.3 H                                                   4-OCF.sub.3 O --CH.sub.3 H                                                    2-F O --CH.sub.3 H                                                            2-OCHF.sub.2 O --CH.sub.3 H                                                   4-Cl -- --CH.sub.3 H                                                          4-CF.sub.3 -- --CH.sub.3 H                                                    2,4-Cl.sub.2 -- --CH.sub.3 H                                                  4-OCF.sub.3 -- --CH.sub.3 H                                                   2-F -- --CH.sub.3 H                                                           2-OCHF.sub.2 -- --CH.sub.3 H                                                  4-Cl CH.sub.2 --C.sub.4 H.sub.9 -n H                                          2,4-Cl.sub.2 CH.sub.2 --CH(CH.sub.3).sub.2 H                                  4-OCF.sub.3 CH.sub.2 --C(CH.sub.3).sub.3 H                                     - 4-Cl CH.sub.2                                                                                                  H TR374##                                  - 4-Cl CH.sub.2                                                                                                  H TR375##                                  - 4-Cl CH.sub.2                                                                                                  H TR376##                                  - 4-Cl CH.sub.2                                                                                                  H TR377##                                  - 2,4,6-Cl.sub.3 CH.sub.2 --CH.sub.3 H                                        -                                                                                                                CH.sub.2 --CH.sub.3 H                      -                                                                                                                --CH.sub.2 --CH.sub.3 H                    - 4-OCF.sub.3 CH.sub.2 --CH.sub.3 H                                        ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                                                       (Ii)                                                                            #STR380##                                       -                                                                          X.sup.4.sub.r                                                                            R.sup.12         R        Y.sup.2                                  ______________________________________                                          2,4-Cl.sub.2                                                                                                       --CH.sub.3 O                              - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 O                                      -- --C(CH.sub.3).sub.3 --CH.sub.3 O                                           4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                          2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         4-F --C(CH.sub.3).sub.3 --CH.sub.3 O                                           -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3 O                                              -                                                                             --C(CH.sub.3).sub.3 --CH.sub.3 O                                              - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                          --CH.sub.3 O                               2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                             3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                         2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                               4-Cl --CH.sub.3 --CH.sub.3 O                                                   - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                  2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                                 4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                   - 2,4-Cl.sub.2                                                                                                    H O 386##                                 - 4-Cl                                                                                                            H O 387##                                 - 4-Br --C(CH.sub.3).sub.3 H O                                               -- --C(CH.sub.3).sub.3 H O                                                    4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 H O                                   2-Cl --C(CH.sub.3).sub.3 H O                                                  3-Cl --C(CH.sub.3).sub.3 H O                                                  4-F --C(CH.sub.3).sub.3 H O                                                    -                                                                                                                 --C(CH.sub.3).sub.3 H O                   -                                                                                                                 --C(CH.sub.3).sub.3 H O                   - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 H O                                       2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 H O                                      3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 H O                                  2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 H O                                        4-Cl --CH.sub.3 H O                                                            - 4-Cl                                                                                                            H O 390##                                 - 4-CF.sub.3 --C(CH.sub.3).sub.3 H O                                         4-OCF.sub.3 --C(CH.sub.3).sub.3 H O                                           2-OCHF.sub.2 --C(CH.sub.3).sub.3 H O                                          4-OCH.sub.3 --C(CH.sub.3).sub.3 H O                                            - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Cl                                                                                                            --CH.sub.3 O                              - 4-Cl                                                                                                            H O 393##                                 - 4-Cl                                                                                                            H O 394##                                 - 2,4-Cl.sub.2                                                                                                    --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                               -- --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                   2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  4-F --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                    -                                                                                                                 --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                    - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                       2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                      3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                  2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                        4-Cl --CH.sub.3 --CH.sub.3 CH.sub.2                                            - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                         4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                           2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                          4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                            - 2,4-Cl.sub.2                                                                                                    H CH.sub.2                                - 4-Cl                                                                                                            H CH.sub.2                                - 4-Br --C(CH.sub.3).sub.3 H CH.sub.2                                        -- --C(CH.sub.3).sub.3 H CH.sub.2                                             4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                            2-Cl --C(CH.sub.3).sub.3 H CH.sub.2                                           3-Cl --C(CH.sub.3).sub.3 H CH.sub.2                                           4-F --C(CH.sub.3).sub.3 H CH.sub.2                                             -                                                                                                                 --C(CH.sub.3).sub.3 H CH.sub.2                                                -                                                                             --C(CH.sub.3).sub.3 H CH.sub.2                                                - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                          H CH.sub.2                                 2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 H CH.sub.2                               3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 H CH.sub.2                           2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                 4-Cl --CH.sub.3 H CH.sub.2                                                     - 4-Cl                                                                                                            H CH.sub.2                                - 4-CF.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                  4-OCF.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                    2-OCHF.sub.2 --C(CH.sub.3).sub.3 H CH.sub.2                                   4-OCH.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                     - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            --CH.sub.3 CH.sub.2                       - 4-Cl                                                                                                            H CH.sub.2                                - 4-Cl                                                                                                            H CH.sub.2                                - 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                      4-Cl --C(CH.sub.3).sub.3 H O                                                ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                                                      (Ik)                                                                            #STR409##                                        -                                                                          X.sup.5.sub.s    A              R                                             ______________________________________                                        2,4-Cl.sub.2     --(CH.sub.2).sub.3 --                                                                        --CH.sub.3                                      2,4-Cl.sub.2 --(CH.sub.2).sub.2 -- --CH.sub.3                                  - 4-Cl                                                                                                       --CH.sub.3                                     - 4-CF.sub.3                                                                                                 --CH.sub.3                                     -                                                                                                            --CH.sub.2 --CH.sub.2 -- --CH.sub.3                                           -                                                                             #STR413##                                                                     --CH.sub.3                                     - 4-F                                                                                                        --CH.sub.3                                     - 4-OCF.sub.3                                                                                                --CH.sub.3                                     - 2,4-F.sub.2                                                                                                --CH.sub.3                                     - 2-OCHF.sub.2                                                                                               --CH.sub.3                                     -                                                                                                            --(CH.sub.2).sub.3 -- --CH.sub.3                                              - 2,4,6-Cl.sub.3                                                              --CH.sub.3                                     - --                                                                                                         --CH.sub.3                                     - 2,4-F.sub.2                                                                                                --CH.sub.3                                     -                                                                                                            #STR423##                                                                     --CH.sub.3                                     - 2,4-Cl.sub.2                                                                                               --CH.sub.3                                     -                                                                                                            #STR426##                                                                     --CH.sub.3                                     - 2,4-Cl.sub.2                                                                                               --CH.sub.3                                     -                                                                                                            #STR429##                                                                     --CH.sub.3                                     - 2,4-Cl.sub.2                                                                                               --CH.sub.3                                     - 2,4-Cl.sub.2 --(CH.sub.2).sub.3 -- H                                       2,4-Cl.sub.2 --(CH.sub.2).sub.2 -- H                                           - 4-Cl                                                                                                       H TR432##                                      - 4-CF.sub.3                                                                                                 H TR433##                                      -                                                                                                            --CH.sub.2 --CH.sub.2 -- H                     -                                                                                                            #STR435##                                                                     H TR436##                                      - 4-F                                                                                                        H TR437##                                      - 4-OCF.sub.3                                                                                                H TR438##                                      - 2,4-F.sub.2                                                                                                H TR439##                                      - 2-OCHF.sub.2                                                                                               H TR440##                                      -                                                                                                            --(CH.sub.2).sub.3 -- H                        - 2,4,6-Cl.sub.3                                                                                             H TR442##                                      - --                                                                                                         H TR443##                                      - 2,4-F.sub.2                                                                                                H TR444##                                      -                                                                                                            #STR445##                                                                     H TR446##                                      - 2,4-Cl.sub.2                                                                                               H TR447##                                      -                                                                                                            #STR448##                                                                     H TR449##                                      - 2,4-Cl.sub.2                                                                                               H TR450##                                      -                                                                                                            #STR451##                                                                     H TR452##                                      - 2,4-Cl.sub.2                                                                                               H TR453##                                      - 2,4-Cl.sub.2                                                                                               --CH.sub.3                                     - 2,4-Cl.sub.2                                                                                               HSTR455##                                   ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                                                   (Im)                                                                            #STR456##                                           -                                                                          X.sup.6.sub.t                                                                            R.sup.13            R                                              ______________________________________                                          2,4-Cl.sub.2 --CH.sub.3 --CH.sub.3                                            2,4-Cl.sub.2 --C.sub.2 H.sub.5 --CH.sub.3                                     2,4-Cl.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.3                                  4-Cl --C.sub.3 H.sub.7 -n --CH.sub.3                                          2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n --CH.sub.3                                   - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3                                2-Cl --C.sub.3 H.sub.7 -n --CH.sub.3                                          2-OCF.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                   4-CF.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                    4-CH.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                    2,4,6-Cl.sub.3 --C.sub.3 H.sub.7 -n --CH.sub.3                                2,4-Cl.sub.2                                                                                                 --CH.sub.3                                     4-F --C.sub.3 H.sub.7 -n --CH.sub.3                                            - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2                                                                                              --CH.sub.3                                      - 2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                                             2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2                                        --CH.sub.3 --CH.sub.3                            4-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                          2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.3 --CH.sub.3                              4-F --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                           2-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 --CH.sub.3                          2,4-Cl.sub.2 --CH.sub.3 H                                                     2,4-Cl.sub.2 --C.sub.2 H.sub.5 H                                              2,4-Cl.sub.2 --CH(CH.sub.3).sub.2 H                                           4-Cl --C.sub.3 H.sub.7 -n H                                                   2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n H                                           2,4-Cl.sub.2                                                                                                 H TR469##                                       - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 H                                         2-Cl --C.sub.3 H.sub.7 -n H                                                   2-OCF.sub.3 --C.sub.3 H.sub.7 -n H                                            4-CF.sub.3 --C.sub.3 H.sub.7 -n H                                             4-CH.sub.3 --C.sub.3 H.sub.7 -n H                                             2,4,6-Cl.sub.3 --C.sub.3 H.sub.7 -n H                                          - 2,4-Cl.sub.2                                                                                              H TR470##                                       - 4-F --C.sub.3 H.sub.7 -n H                                                  - 2,4-Cl.sub.2                                                                                              H TR471##                                       - 2,4-Cl.sub.2                                                                                              H TR472##                                       - 2,4-Cl.sub.2                                                                                              H TR473##                                       - 2,4-Cl.sub.2                                                                                              H TR474##                                       - 2,4-Cl.sub.2                                                                                              H TR475##                                       - 2,4-Cl.sub.2                                                                                              H TR476##                                       - 2,4-Cl.sub.2                                                                                              H TR477##                                       - 2,4-Cl.sub.2                                                                                              H TR478##                                       - 2,4-Cl.sub.2                                                                                              H TR479##                                       - 2,4-Cl.sub.2                                                                                              H TR480##                                       - 2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 H                        2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.2 --CH.sub.3 H                            4-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 H                                   2,4-Cl.sub.2 --CH.sub.2 --O--CF.sub.3 H                                       4-F --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 H                                    2-Cl --CH.sub.2 --O--CF.sub.2 --CHF.sub.2 H                                   2,4-Cl.sub.2 --CH.sub.2 --CF.sub.3 --CH.sub.3                                 2,4-Cl.sub.2 --CF.sub.2 --CF.sub.3 --CH.sub.3                                 2,4-Cl.sub.2 --C.sub.3 H.sub.7 -n --CH.sub.3                                  2,4-Cl.sub.2 --C.sub.3 H.sub.7 -n H                                         ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                                                    (In)                                                                            #STR481##                                          -                                                                          X.sup.7.sub.u                                                                              R.sup.14        R        Y.sup.3                                 ______________________________________                                          2,4-Cl.sub.2                                                                                                        --CH.sub.3 O                             - 4-Cl                                                                                                             --CH.sub.3 O                             - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 O                                      -- --C(CH.sub.3).sub.3 --CH.sub.3 O                                           4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                          2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                         4-F --C(CH.sub.3).sub.3 --CH.sub.3 O                                           -                                                                                                                  --C(CH.sub.3).sub.3 --CH.sub.3 O                                              -                                                                             --C(CH.sub.3).sub.3 --CH.sub.3 O                                              - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                           --CH.sub.3 O                             2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                             3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                         2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                               4-Cl --CH.sub.3 --CH.sub.3 O                                                   - 4-Cl                                                                                                             --CH.sub.3 O                             - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                  2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 O                                 4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 O                                   - 2,4-Cl.sub.2                                                                                                     H O 487##                                - 4-Cl                                                                                                             H O 488##                                - 4-Br --C(CH.sub.3).sub.3 H O                                               -- --C(CH.sub.3).sub.3 H O                                                    4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 H O                                   2-Cl --C(CH.sub.3).sub.3 H O                                                  3-Cl --C(CH.sub.3).sub.3 H O                                                  4-F --C(CH.sub.3).sub.3 H O                                                    -                                                                                                                  --C(CH.sub.3).sub.3 H O                  -                                                                                                                  --C(CH.sub.3).sub.3 H O                 2,4-Cl.sub.2 --C(CH.sub.3).sub.3 H O                                          2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 H O                                      3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 H O                                  2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 H O                                        4-Cl --CH.sub.3 H O                                                            - 4-Cl                                                                                                             H O 491##                                - 4-CF.sub.3 --C(CH.sub.3).sub.3 H O                                         4-OCF.sub.3 --C(CH.sub.3).sub.3 H O                                           2-OCHF.sub.2 --C(CH.sub.3).sub.3 H O                                          4-OCH.sub.3 --C(CH.sub.3).sub.3 H O                                            - 4-Cl                                                                                                             --CH.sub.3 O                             - 4-Cl                                                                                                             --CH.sub.3 O                             - 4-Cl                                                                                                             H O 494##                                - 4-Cl                                                                                                             H O 495##                                - 2,4-Cl.sub.2                                                                                                     --CH.sub.3 CH.sub.2                      - 4-Cl                                                                                                             --CH.sub.3 CH.sub.2                      - 4-Br --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                               -- --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                   2-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  3-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                  4-F --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                                    -                                                                                                                  --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                   -                                                                                                                  --C(CH.sub.3).sub.3 --CH.sub.3                                              CH.sub.2                                   - 2,4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                             2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                      3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                  2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                        4-Cl --CH.sub.3 --CH.sub.3 CH.sub.2                                            - 4-Cl                                                                                                             --CH.sub.3 CH.sub.2                      - 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                         4-OCF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                           2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                          4-OCH.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3 CH.sub.2                            - 2,4-Cl.sub.2                                                                                                     H CH.sub.2                               - 4-Cl                                                                                                             H CH.sub.2                               - 4-Br --C(CH.sub.3).sub.3 H CH.sub.2                                        -- --C(CH.sub.3).sub.3 H CH.sub.2                                             4-C(CH.sub.3).sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                            2-Cl --C(CH.sub.3).sub.3 H CH.sub.2                                           3-Cl --C(CH.sub.3).sub.3 H CH.sub.2                                           4-F --C(CH.sub.3).sub.3 H CH.sub.2                                             -                                                                                                                  --C(CH.sub.3).sub.3 H CH.sub.2                                                -                                                                             --C(CH.sub.3).sub.3 H CH.sub.2                                                - 2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                           H CH.sub.2                               2-CH.sub.3, 4-Cl --C(CH.sub.3).sub.3 H CH.sub.2                               3,4-(CH.sub.3).sub.2 --C(CH.sub.3).sub.3 H CH.sub.2                           2,4,5-Cl.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                 4-Cl --CH.sub.3 H CH.sub.2                                                     - 4-Cl                                                                                                             H CH.sub.2                               - 4-CF.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                  4-OCF.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                    2-OCHF.sub.2 --C(CH.sub.3).sub.3 H CH.sub.2                                   4-OCH.sub.3 --C(CH.sub.3).sub.3 H CH.sub.2                                     - 4-Cl                                                                                                             --CH.sub.3 CH.sub.2                      - 4-Cl                                                                                                             --CH.sub.3 CH.sub.2                      - 4-Cl                                                                                                             H CH.sub.2                               - 4-Cl                                                                                                             H CH.sub.2                               - 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3 O                                      4-Cl --C(CH.sub.3).sub.3 H O                                                ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                                                    (Ip)                                                                            #STR510##                                          -                                                                          X.sup.8.sub.v                                                                            R.sup.15              R                                            ______________________________________                                          4-Cl --C.sub.4 H.sub.9 -n --CH.sub.3                                          2-Cl --C.sub.4 H.sub.9 -n --CH.sub.3                                          2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n --CH.sub.3                                  4-Br --C.sub.4 H.sub.9 -n --CH.sub.3                                          4-F --C.sub.4 H.sub.9 -n --CH.sub.3                                           4-C(CH.sub.3).sub.3 --C.sub.4 H.sub.9 -n --CH.sub.3                            -                                                                                                             --C.sub.4 H.sub.9 -n --CH.sub.3                                               - 4-Cl --C(CH.sub.3).sub.3 --CH.sub.3                                        2-Cl --C(CH.sub.3).sub.3 --CH.sub.3                                           2,4-Cl.sub.2 --C(CH.sub.3).sub.3                                             --CH.sub.3                                     2,4,6-Cl.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3                                 4-CF.sub.3 --C(CH.sub.3).sub.3 --CH.sub.3                                     2-OCHF.sub.2 --C(CH.sub.3).sub.3 --CH.sub.3                                   4-Cl                                                                                                           --CH.sub.3                                    - 4-Cl                                                                                                        --CH.sub.3                                    - 4-Cl                                                                                                        --CH.sub.3                                    - 4-Cl                                                                                                        --CH.sub.3                                    - 4-Cl                                                                                                        --CH.sub.3                                    - 4-Cl                                                                                                        --CH.sub.3                                    - --                                                                                                          --CH.sub.3                                    - 4-Cl --C.sub.4 H.sub.9 -n H                                                2-Cl --C.sub.4 H.sub.9 -n H                                                   2,4-Cl.sub.2 --C.sub.4 H.sub.9 -n H                                           4-Br --C.sub.4 H.sub.9 -n H                                                   4-F --C.sub.4 H.sub.9 -n H                                                    4-C(CH.sub.3).sub.3 --C.sub.4 H.sub.9 -n H                                     -                                                                                                             --C.sub.4 H.sub.9 -n H                        - 4-Cl --C(CH.sub.3).sub.3 H                                                 2-Cl --C(CH.sub.3).sub.3 H                                                    2,4-Cl.sub.2 --C(CH.sub.3).sub.3 H                                            2,4,6-Cl.sub.3 --C(CH.sub.3).sub.3 H                                          4-CF.sub.3 --C(CH.sub.3).sub.3 H                                              2-OCHF.sub.2 --C(CH.sub.3).sub.3 H                                             - 4-Cl                                                                                                        H TR520##                                     - 4-Cl                                                                                                        H TR521##                                     - 4-Cl                                                                                                        H TR522##                                     - 4-Cl                                                                                                        H TR523##                                     - 4-Cl                                                                                                        H TR524##                                     - 4-Cl                                                                                                        H TR525##                                     - --                                                                                                          H TR526##                                     - --                                                                                                          H TR527##                                     - --                                                                                                          --CH.sub.3                                 ______________________________________                                    

If2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(imidazol-1-yl)-propan-2-olis used as the starting material, n-butyl-lithium as the strong base andsulphur powder as reactant, the course of the first step of the processaccording to the invention (variant a) can be illustrated by thefollowing scheme: ##STR529##

If2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(imidazol-1-yl)-propan-2-olis used as the starting material, sulphur powder as reactant andN-methyl-pyrrolidone as diluent, the course of the first step of theprocess according to the invention (variant b) can be illustrated by thefollowing scheme: ##STR530##

If2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(2-mercapto-imidazol-1-yl)-propan-2-olis used as the starting material and methyl iodide as reactant, thecourse of the second step of the process according to the invention canbe illustrated by the following scheme: ##STR531##

Formula (II) provides a general definition of the imidazoles required asstarting materials for carrying out the process according to theinvention. In this formula, R¹ preferably has those meanings which havealready been mentioned in connection with the description of thesubstances of the formula (I) according to the invention as beingpreferred for this radical.

The imidazoles of the formula (II) are known or can be prepared by knownmethods (cf. EP-A 0 015 756, EP-A 0 040 345, EP-A 0 052 424, EP-A 0 061835, EP-A 0 297 345, EP-A 0 094 564, EP-A 0 196 038, EP-A 0 267 778,EP-A 0 378 953, EP-A 0 044 605, EP-A 0 069 442, EP-A 0 055 833, EP-A 0301 393, DE-A 2 324 010, DE-A 2 737 489, DE-A 2 551 560, EP-A 0 065 485,DE-A 2 735 872, EP-A 0 234 242, DE-A 2 201 063, EP-A 0 145 294 and DE-A3 721 786).

Suitable bases for carrying out the first step of the process accordingto the invention (variant a) are all strong alkali metal bases which arecustomary for such reactions. The following can preferably be used:n-butyl-lithium, lithium diisopropyl-amide, sodium hydride, sodium amideor else potassium tert-butoxide as a mixture withtetramethylethylene-diamine (=TMEDA).

Suitable diluents for carrying out the first step of the processaccording to the invention (variant a) are all inert organic solventswhich are customary for such reactions. The following can preferably beused: ethers such as tetrahydrofuran, dioxane, diethyl ether and1,2-dimethoxyethane, furthermore liquid ammonia or else strongly polarsolvents such as dimethyl sulphoxide.

Sulphur is preferably employed in the form of a powder. Water, ifappropriate in the presence of an acid, is used for the hydrolysis whencarrying out the first step of the process according to the invention(variant a). Suitable for this purpose are all inorganic or organicacids which are customary for such reactions. The following canpreferably be used: acetic acid, dilute sulphuric acid and dilutehydrochloric acid. However, it is also possible to carry out thehydrolysis with aqueous ammonium chloride solution.

When carrying out the first step of the process according to theinvention (variant a), the reaction temperatures can be varied within acertain range. In general, the process is carried out at temperaturesbetween -70° C. and +20° C., preferably between -70° C. and 0° C.

All steps of the process according to the invention are generallycarried out under atmospheric pressure. However, it is also possible tocarry out these steps under elevated or reduced pressure. In particular,the first step of the process according to the invention in accordancewith variant (b) may be carried out under elevated pressure.

When carrying out the first step of the process according to theinvention in accordance with variant (a), 2 to 3 equivalents, preferably2.0 to 2.5 equivalents, of strong base and subsequently an equivalentamount or else an excess of sulphur are generally employed per mole ofimidazole of the formula (II). The reaction can be carried out underprotective gas atmosphere, for example under nitrogen or argon.Working-up is carried out by customary methods. In general, a procedureis followed in which the reaction mixture is extracted with an organicsolvent which is sparingly soluble in water, the combined organic phasesare dried and concentrated, and, if appropriate, the residue whichremains is purified by recrystallization and/or chromatography.

When carrying out the first step of the process according to theinvention in accordance with variant (b), suitable diluents are allorganic solvents of high boiling point which are customary for suchreactions. The following can preferably be used: amides such asdimethylformamide and dimethylacetamide, furthermore heterocycliccompounds such as N-methyl-pyrrolidone, or else ethers such as diphenylether.

When carrying out the first step of the process according to theinvention in accordance with variant (b), sulphur is, again, generallyemployed in the form of a powder. If appropriate, a treatment with waterand, if appropriate, with acid may be carried out after the reaction.This treatment is carried out like the hydrolysis when carrying out thefirst step of the process according to the invention in accordance withvariant (a).

When carrying out the first step of the process according to theinvention in accordance with variant (b), the reaction temperatures can,again, be varied within a substantial range. In general, the process iscarried out at temperatures between 150° C. and 300° C., preferablybetween 180° C. and 250° C.

When carrying out the first step of the process according to theinvention in accordance with variant (b), 1 to 5 mol, preferably 1.5 to3 mol, of sulphur are generally employed per mole of imidazole of theformula (II). Working-up is carried out by customary methods. Ingeneral, a procedure is followed in which the reaction mixture isextracted with an organic solvent which is only sparingly soluble inwater, the combined organic phases are dried and concentrated, and, ifappropriate, the residue which remains is freed from any impuritieswhich may be present by customary methods, such as recrystallization orchromatography.

The compounds of the formula (la) required as starting materials whencarrying out the second step of the process according to the inventionare substances according to the invention.

Formula (III) provides a general definition of the halogen compoundsrequired as reactants when carrying out the second step of the processaccording to the invention.

R16 preferably represents methyl, ethyl, n-propyl or isopropyl.

HaI preferably represents chlorine, bromine or iodine.

R¹⁶ especially preferably represents methyl or ethyl.

HaI especially preferably represents bromine or iodine.

The halogen compounds of the formula (III) are known.

Suitable acid binders for carrying out the second step of the processaccording to the invention are all customary inorganic or organic bases.The following can preferably be used: alkaline earth metal hydroxides oralkali metal hydroxides such as sodium hydroxide, calcium hydroxide,potassium hydroxide, or else ammonium hydroxide, alkali metal carbonatessuch as sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogen carbonate, alkali metal acetates or alkalineearth metal acetates such as sodium acetate, potassium acetate, calciumacetate, and tertiary amines such as trimethylamine, triethylamine,tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Diluents which are suitable for carrying out the second step of theprocess according to the invention are all inert organic solvents whichare customary for such reactions. The following can preferably be used:ethers such as diethyl ether, methyl tert-butyl ether, ethylene glycoldimethyl ether, tetrahydrofuran and dioxane, furthermore nitriles suchas acetonitrile, and also strongly polar solvents such as dimethylsulphoxide or dimethylformamide.

When carrying out the second step of the process according to theinvention, the reaction temperatures can be varied within a substantialrange. In general, the process is carried out at temperatures between 0°C. and 120° C., preferably between 20° C. and 100° C.

When carrying out the second step of the process according to theinvention, 1 to 2 mol of halogen compound of the formula (III) and anequivalent amount or else an excess of acid binder are generallyemployed per mole of mercapto-imidazolyl derivative of the formula (Ia).Working-up is carried out by customary methods. In general, a procedureis followed in which the reaction mixture is treated with aqueous baseand an organic solvent which is sparingly miscible with water, and theorganic phase is separated off, dried and concentrated. If appropriate,the product obtained can be freed from any impurities which may bepresent by customary methods, for example by recrystallization.

The mercapto-imidazolyl derivatives of the formula (I) which can beobtained by the process according to the invention can be converted intoacid addition salts or metal salt complexes.

Acids which are suitable for the preparation of acid addition salts ofthe compounds of the formula (I) are preferably those which have alreadybeen mentioned as preferred acids in connection with the description ofthe acid addition salts according to the invention.

The acid addition salts of the compounds of the formula (I) can beobtained in a simple manner by customary salt formation methods, forexample by dissolving a compound of the formula (I) in a suitable inertsolvent and adding the acid, for example hydrochloric acid, and they canbe isolated in a known manner, for example by filtration, and, ifappropriate, purified by washing with an inert organic solvent. Metalsalts which are suitable for the preparation of metal salt complexes ofthe compounds of the formula (I) are preferably those which have alreadybeen mentioned as preferred metal salts in connection with thedescription of the metal salt complexes according to the invention.

The metal salt complexes of the compounds of the formula (I) can beobtained in a simple manner by customary methods, for example bydissolving the metal salt in alcohol, for example ethanol, and addingthe solution to compounds of the formula (I). Metal salt complexes canbe isolated in a known manner, for example by filtration, and, ifappropriate, purified by recrystallization.

The active compounds according to the invention exhibit a potentmicrobicidal action and can be employed in crop protection and in theprotection of materials for controlling undesired microorganisms such asfungi and bacteria.

Fungicides are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides are employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some causative organisms of fungal and bacterial diseases which comeunder the generic names listed above may be mentioned as examples, butnot by way of limitation:

Xanthomonas species, such as Xanthomonas oryzae;

Pseudomonas species, such as Pseudomonas lachrymans;

Erwinia species, such as Erwinia amylovora;

Pythium species, such as Pythium ultimum;

Phytophthora species, such as Phytophthora infestans;

Pseudoperonospora species, such as Pseudoperonospora humuli orPseudoperonospora cubensis;

Plasmopara species, such as Plasmopara viticola;

Peronospora species, such as Peronospora pisi or P. brassicae;

Erysiphe species, such as Erysiphe graminis;

Sphaerotheca species, such as Sphaerotheca fuliginea;

Podosphaera species, such as Podosphaera leucotricha;

Venturia species, such as Venturia inaequalis;

Pyrenophora species, such as Pyrenophora teres or P. graminea;

(conidial form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as Cochliobolus sativus;

(conidial form: Drechslera, syn: Helminthosporium);

Uromyces species, such as Uromyces appendiculatus;

Puccinia species, such as Puccinia recondita;

Tilletia species, such as Tilletia caries;

Ustilago species, such as Ustilago nuda or Ustilago avenae;

Pellicularia species, such as Pellicularia sasakii;

Pyricularia species, such as Pyricularia oryzae;

Fusarium species, such as Fusarium culmorum;

Botrytis species, such as Botrytis cinerea;

Septoria species, such as Septoria nodorum;

Leptosphaeria species, such as Leptosphaeria nodorum;

Cercospora species, such as Cercospora canescens;

Altemaria species, such as Altemaria brassicae;

Pseudocercosporella species, such as Pseudocercosporellaherpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for controlling plant diseases, permitstreatment of above-ground parts of plants, of vegetative propagationstock and seeds, and of the soil.

The active compounds according to the invention are particularlysuitable for controlling Pyricularia oryzae and Pellicularia sasakii onrice and for controlling cereal diseases such as Pseudocercosporella,Erysiphe and Fusarium species. In addition, the substances according tothe invention can be employed very successfully against Venturia andSphaerotheca. Moreover, they also have a very good in vitro action.

In the protection of materials, the substances according to theinvention can be employed for protecting industrial materials againstinfestation with, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-live materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be glues, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infested with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the multiplication of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably glues, sizes, papers and boards, leather, wood,paints, cooling lubricants and heat-transfer liquids, especiallypreferably wood. Microorganisms which may be mentioned as being capableof bringing about degradation of, or change in, the industrial materialsare, for example, bacteria, fungi, yeasts, algae and slime organisms.The active compounds according to the invention preferably act againstfungi, in particular moulds, wood-discolouring and wood-destroying fungi(Basidiomycetes) and against slime organisms and algae.

Microorganisms of the following genera may be mentioned as examples:

Altemaria, such as Altemaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, very fine capsules in polymeric substances and in coatingcompositions for seed, and ULV cold and hot fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is emulsifiers and/or dispersants, and/orfoam formers. In the case of the use of water as an extender, organicsolvents can, for example, also be used as auxiliary solvents. The mainliquid solvents suitable are: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample mineral oil fractions, alcohols, such as butanol or glycol aswell as their ethers and esters, ketones, such as acetone, methyl ethylketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents, such as dimethylformamide and dimethyl sulphoxide, as well aswater; by liquefied gaseous extenders or carriers are meant liquidswhich are gaseous at ambient temperature and under atmospheric pressure,for example aerosol propellants such as butane, propane, nitrogen andcarbon dioxide; suitable solid carriers are: for example ground naturalminerals, such as kaolins, clays, talc, chalk, quartz, attapulgite,montmorillonite or diatomaceous earth, and ground synthetic minerals,such as highly-disperse silica, alumina and silicates; suitable solidcarriers for granules are: for example crushed and fractionated naturalrocks such as calcite, marble, pumice, sepiolite and dolomite, as wellas synthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; suitable emulsifiers and/or foam formers are: for examplenon-ionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxy-methylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Further additives may bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%. When used incrop protection, the active compounds according to the invention, assuch or in their formulations, can also be used as a mixture with knownfungicides, bactericides, acaricides, nematicides or insecticides, forexample to widen the spectrum of action or to prevent the build-up ofresistance. In many cases, synergistic effects are obtained, i.e. theactivity of the mixture is greater than the activity of the individualcomponents.

Examples of suitable components in mixtures are the followingsubstances.

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thizole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione,isoprothiolane,

kasugamycin, copper preparations such as: copper hydroxide, coppernaphthenate, copper oxychloride, copper sulphate, copper oxide,oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax,myclobutanil,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin,polyoxin, probenazole, prochloraz, procymidone, propamocarb,propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,pyroquilon,

quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, toiclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumizole, triforine, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,beta-cyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulfotep, suiprofos,

tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, zetamethrin.

A mixture with other known active compounds such as herbicides, or withfertilizers and growth regulators, is also possible.

The active compounds can be used as such, in the form of theirformulations or as the use forms prepared therefrom, such asready-to-use solutions, emulsifiable concentrates, emulsions, foams,suspensions, wettable powders, pastes, soluble powders, dusts andgranules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering, dusting, foaming, brushing onand the like. It is furthermore possible to apply the active compoundsby the ultra-low volume method, or to inject the active compoundpreparation or the active compound itself into the soil. The seed of theplants can also be treated.

For the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range: they aregenerally between 1 and 0.0001% by weight, preferably between 0.5 and0.001% by weight.

For the treatment of seed, amounts of active compound of 0.001 to 50 g,preferably 0.01 to 10 g, are generally required per kilogram of seed.

For the treatment of the soil, active compound concentrations of 0.00001to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required atthe site of action.

The compositions used for the protection of industrial materialsgenerally comprise the active ingredients in an amount of 1 to 95%,preferably 10 to 75%.

The use concentrations of the active compounds according to theinvention depend on the species and the occurrence of the microorganismsto be controlled and on the composition of the material to be protected.The optimal rate can be determined by test series. In general, the useconcentrations are in the range from 0.001 to 5% by weight, preferably0.05 to 1.0% by weight, based on the material to be protected.

The activity and spectrum of action of the active compounds to be usedaccording to the invention in the protection of materials, or of thecompositions, concentrates or, quite generally, formulations which canbe prepared therefrom, can be increased when, if appropriate, otherantimicrobially active compounds, fungicides, bactericides, herbicides,insecticides or other active compounds for widening the spectrum ofaction or achieving specific effects, such as, for example, anadditional protection against insects, are added. These mixtures mayhave a wider spectrum of action than the compounds according to theinvention.

The preparation and use of the substances according to the invention canbe seen from the examples which follow.

PREPARATION EXAMPLES Example 1 ##STR532##

A mixture of 1.55 g (5 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(imidazol-1-yl)-propan-2-ol,0.32 g (0.01 gram atom) of sulphur powder and 20 ml of absoluteN-methyl-pyrrolidone is heated for 3 hours at 200° C. with stirring. Thereaction mixture is subsequently diluted with ethyl acetate andextracted repeatedly by shaking with saturated aqueous ammonium chloridesolution. Then, the organic phase is dried over sodium sulphate andconcentrated under reduced pressure. The product which remains ischromatographed on silica gel using petroleum ether/ethyl acetate=1:1 asmobile phase. After the eluate has been concentrated, 0.6 g (35% oftheory) of2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(2-mercapto-imidazol-1-yl)-propan-2-olis obtained in the form of a solid of melting point 124 to 126° C.

¹ H NMR spectrum (200 MHz; CDCl₃ ; TMS):δ=0.6-1.1 (m,4H); 3.0 (d.1H);3.75 (d,1H); 4.4 (AB,2H); 5.15 (OH); 6.7 (1H); 7.05 (1H); 7.2-7.6(m,4H); 10.25 (1H) ppm.

Preparation of the starting material ##STR533##

A mixture of 5.56 g (20 mmol) of3-chloro-2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-propan-2-ol, 1.36g (20 mmol) of imidazole and 4.15 g (30 mmol) of anhydrous potassiumcarbonate in 30 ml of absolute dimethylformamide is heated for 23 hoursat 100° C. with stirring. The reaction mixture is subsequently dilutedwith ethyl acetate and extracted repeatedly with saturated aqueousammonium chloride solution. Then, the organic phase is dried over sodiumsulphate and concentrated under reduced pressure. The product whichremains is chromatographed on silica gel using ethyl acetate as themobile phase. After the eluate has been concentrated under reducedpressure, 1.7 g (27% of theory) of2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(imidazol-1-yl)-propan-2-olare obtained in the form of a solid of melting point 136 to 139° C.

¹ H NMR spectrum (400 MHz; CDCl₃ ; TMS):δ=0.5-0.8 (m,4H); 3.3 (d, 1H);3.45 (d,1H); 4.0 (d,1H); 4.6 (d,1H); 7.0 (m,2H); 7.25-7.5 (m,4H); 7.55(s,1H) ppm.

Example A

Erysiphe test (barley)/protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the given rate of application.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of approx. 20° C.and a relative atmospheric humidity of approx. 80%, in order to promotethe development of powdery mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no disease is observed.

Active compounds, active compound concentrations and test results can beseen from the table which follows.

                  TABLE A                                                         ______________________________________                                        Erysiphe test (barley)/protective                                                                     Rate of application                                      of active Efficacy                                                           Active compound compound in g/ha in %                                       ______________________________________                                        According to the invention:                                                                                      250 834##                                  ______________________________________                                    

Example B

Sphaerotheca test (cucumber)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the given rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspejnsion of Sphaerotheca fuliginea. The plants areplaced in a greenhouse at approx. 23° C. and at a relative atmospherichumidity of approx. 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while 100% means thatno disease is observed.

Active compounds, active compound concentrations and test results can beseen from the table which follows.

                  TABLE B                                                         ______________________________________                                        Sphaerotheca test (cucumber)/protective                                                               Rate of application                                      of active Efficacy                                                           Active compound compound in g/ha in %,                                      ______________________________________                                        According to the invention:                                                                                      100 775##                                  ______________________________________                                    

Example C

Venturia test (apple)/protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkyl-aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the given rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous conidial suspension of the apple scab causative organismVenturia inaequalis and then remain in an incubation cabin at approx.20° C. and 100% relative atmospheric humidity for 1 day.

The plants are then placed in a greenhouse at 21° C. and a relativeatmospheric humidity of approx. 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while 100% means thatno disease is observed.

Active compounds, active compound concentrations and test results can beseen from the table which follows.

                  TABLE C                                                         ______________________________________                                        Venturia test (apple)/protective                                                                      Rate of application                                      of active Efficacy                                                           Active compound compound in g/ha in %                                       ______________________________________                                        According to the invention:                                                                                      50 7936##                                  ______________________________________                                    

What is claimed is:
 1. A mercapto-imidazole compound of the formula##STR537## wherein R represents hydrogen or an alkyl having 1 to 4carbon atoms, andR¹ represents a radical of the formula ##STR538##wherein R² represents straight-chain or branched alkyl having 1 to 6carbon atoms, which is unsubstituted or monosubstituted totetrasubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety andcycloalkyl having 3 to 7 atoms, orrepresents cycloalkyl having 3 to 7carbon atoms, which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, cyano and alkyl having 1 to 4 carbon atoms,or represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and1 to 4 carbon atoms in the straight-chain or branched alkyl moiety,wherein the aryl moiety is unsubstituted or monosubstituted totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano, or represents aroxyalkyl having 6 to 10carbon atoms in the aryl moiety and 1 to 4 carbon atoms in thestraight-chain or branched oxyalkyl moiety, wherein the aryl moiety isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen,alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms,alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms, cycloalkyl having 3 to 7 carbon atoms,phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxymoiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moietyand 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, orrepresents aryl having 6 to 10 carbon atoms, which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atom, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and cyano, or represents anunfused or benzo-fused, five- or six-membered heteroaromatic radicalhaving 1 to 3 hetero atoms selected from the group consisting of sulphurand oxygen, which is unsubstituted or monosubstituted to trisubstitutedby identical or different substituents selected from the groupconsisting of halogen, alkyl having 1 to 4 carbon atoms, hydroxyalkylhaving 1 to 4 carbon atoms, hydroxyalkinyl having 3 to 8 carbon atoms,alkoxy having 1 or 2 carbon atoms, alkylthio having 1 or 2 carbon atoms,halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each of which has 1or 2 carbon atoms and 1 to 5 identical or different halogen atomsselected from the group consisting of fluorine and chlorine atoms,formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxy group,acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety, nitroand cyano, and R³ represents straight-chain or branched alkyl having 1to 6 carbon atoms, which is unsubstituted or monosubstituted totetrasubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety andcycloalkyl having 3 to 7 carbon atoms, or represents cycloalkyl having 3to 7 carbon atoms, which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, cyano and alkyl having 1 to 4 carbon atoms,or represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and1 to 4 carbon atoms in the straight-chain or branched alkyl moiety,wherein the aryl moiety is unsubstituted or monosubstituted totrisubstituted by identical or different substituents selected from thegroup consisting of halogen atoms, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano, or represents aroxyalkyl having 6 to 10carbon atoms in the aryl moiety and 1 to 4 carbon atoms in thestraight-chain or branched oxyalkyl moiety, wherein the aryl moiety isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen,alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms,alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbonatoms and 1 to 5 identical or different halogen atoms, halogenoalkoxyhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms, cycloalkyl having 3 to 7 carbon atoms,phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxymoiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moietyand 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, orrepresents aryl having 6 to 10 carbon atoms, which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and cyano, or represents anunfused or benzo-fused, five- or six-membered heteroaromatic radicalhaving 1 to 3 hetero atoms selected from the group consisting ofnitrogen, sulphur and oxygen, which is unsubstituted or monosubstitutedto trisubstituted by identical or different substituents selected fromthe group consisting of halogen, alkyl having 1 to 4 carbon atoms,hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinyl having 3 to 8carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 or 2carbon atoms, halogenoalkyl, halogenoalkoxy and halogenoalkylthio, eachof which has 1 or 2 carbon atoms and 1 to 5 identical or differenthalogen atoms such as fluorine or chlorine atoms, formyl, dialkoxymethylhaving 1 or 2 carbon atoms in each alkoxy group, acyl having 2 to 4carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxymoiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moietyand 1 to 3 carbon atoms in the alkyl moiety, nitro and cyano, or itsacid addition salts or metal salt complexes.
 2. A mercapto-imidazolecompound of the formula (I-1) ##STR539##
 3. A process for thepreparation of a mercapto-imidazolyl compound of the formula (I) ofclaim 1, or of its acid addition salts or metal salt complexes,comprising the steps of reacting an imidazole of the formula (II)whereinR¹ is as defined in claim 1, either a) in succession with astrong base and sulphur in the presence of a diluent, and thenhydrolyzing the product with water, or b) with sulphur in the presenceof a diluent having a high boiling point; and reacting the product ofvariant a) or b) of the formula (Ia) ##STR540## wherein R¹ is as definedin claim 1, with a halogen compound of the formula (III)

    R.sup.16 --HaI

wherein R¹⁶ represents an alkyl having 1 to 4 carbon atoms, and HaIrepresents chlorine, bromine or iodine,in the presence of an acid binderand in the presence of a diluent.
 4. The process of claim 3 wherein thereaction in variant a) is carried out in th, presence of an acid.
 5. Theprocess of claim 3 wherein variant b) further comprises the step ofhydrolyzing the product with water.
 6. The process of claim 3 whereinvariant b) further comprises the step of hydrolyzing the product with anacid.
 7. A microbicidal composition comprising a microbicidallyeffective amount of a compound or its acid addition salt or metal saltcomplex as claimed in claim 1 and an inert diluent.
 8. A method forcontrolling undesired microorganisms in plant protection and in thepreservation of materials, which method comprises applying to suchundesired microorganisms or to their habitat a microbicidally effectiveamount of a compound or its acid addition salt or metal salt complex asclaimed in claim
 1. 9. The process of claim 3 further comprising thestep of reacting the compounds of the formula (I) with an acid or ametal salt.